Updated on 2024/02/01

写真a

 
FUKUZAWA Shin-ichi
 
Organization
Faculty of Science and Engineering Professor
Other responsible organization
Applied Chemistry Course of Graduate School of Science and Engineering, Master's Program
Applied Chemistry Course of Graduate School of Science and Engineering, Doctoral Program
External link

Degree

  • 工学博士 ( 京都大学 )

Education

  • 1984.3
     

    Kyoto University   Graduate School, Division of Engineering   Department of Hydrocarbon Chemistry   doctor course   completed

Research History

  • 1999.4 -  

    中央大学理工学部教授

  • 1999.4 -  

    ~ 中央大学理工学部教授

  • 1991.4 - 1999.3

    中央大学理工学部助教授   Faculty of Science and Engineering

  • 1984.4 - 1991.3

    静岡大学工学部助手   Faculty of Engineering

Professional Memberships

  • アメリカ化学会

  • 日本化学会

Research Interests

  • catalyst design and reaction

  • organometallic chemistry

  • synthetic organic chemistry

  • 合成有機化学

Research Areas

  • Nanotechnology/Materials / Structural organic chemistry and physical organic chemistry  / Organic Chemistry

  • Life Science / Bioorganic chemistry  / Organic Chemistry

  • Nanotechnology/Materials / Synthetic organic chemistry  / Synthetic Organic Chemistry

Papers

  • Chiral Silver Complex-Catalyzed Asymmetric Conjugate Addition of 1-Pyrroline-5-Carbonitrile to α-Enones Reviewed

    Haruna Araki, Shohei Furuya, Kazuya Kanemoto, Shin-ichi Fukuzawa

    The Journal of Organic Chemistry   88 ( 2 )   924 - 932   2023.1

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    Authorship:Corresponding author   Language:English   Publishing type:Research paper (scientific journal)   Publisher:American Chemical Society (ACS)  

    DOI: 10.1021/acs.joc.2c02315

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  • exo′ ‐Selective Construction of Spirobipyrrolidines by the Silver‐catalyzed Asymmetric [3+2] Cycloaddition of Imino Esters with 4‐Benzylidene‐2,3‐dioxopyrrolidines

    Shohei Furuya, Kazuya Kanemoto, Shin‐ichi Fukuzawa

    Chemistry – An Asian Journal   17 ( 15 )   2022.5

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    Authorship:Corresponding author   Language:English   Publishing type:Research paper (scientific journal)   Publisher:Wiley  

    DOI: 10.1002/asia.202200239

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    Other Link: https://onlinelibrary.wiley.com/doi/full-xml/10.1002/asia.202200239

  • N-(N-Morpholindithio)phthalimide: A Shelf-Stable, Bilateral Platform Molecule for Accessing Diverse Unsymmetrical Disulfides

    Hayato Asanuma, Kazuya Kanemoto, Tokiharu Watanabe, Shin-ichi Fukuzawa

    2022.5

  • Trifluoroacetic Acid-Mediated Desulfurilative Sulfonylation of Activated Olefines Using Potassium p-Toluenethiosulfonate Reviewed

    Watanabe, Tokiharu, Kanemoto, Kazuya, Fykuzawa, Shin-ichi

    Journal of the Institute of Science and Engineering   27   15 - 33   2022.3

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    Language:English   Publishing type:Research paper (bulletin of university, research institution)   Publisher:Institute of Science and Engineering  

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  • 5,5’-ジエチニルインジゴ類およびそのGlaserカップリング反応によるポリマーの合成と性質 Reviewed

    劔持智志, 金本和也, 池田富樹, 福澤信一

    中央大学理工学研究所論文集   27   35 - 46   2022.3

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  • Silver/ThioClickFerrophos-Catalyzed 1,3-Dipolar Cycloaddition and Tandem Addition-Elimination Reaction of Morita-Baylis-Hillman Adducts Reviewed

    Suzuki, Yuko, Kanemoto, Kazuya, Inoue, Ayana, Imae, Kazumi, Fukuzawa, Shin-ichi

    Journal of Organic Chemistry 2021, 86, 14586-14596.   86 ( 21 )   14586 - 14596   2021.11

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:American Chemical Society  

    DOI: 10.1021/acs.joc.1c01440

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  • Copper-Catalyzed Single C–H Amination of 8-Aminoquinoline-Directed Ferrocenes

    Kazuya Kanemoto, Nao Horikawa, Shun Hoshino, Yuichiro Tokoro, Shin-ichi Fukuzawa

    Organic Letters   23 ( 13 )   4966 - 4970   2021.7

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    Publishing type:Research paper (scientific journal)   Publisher:American Chemical Society (ACS)  

    DOI: 10.1021/acs.orglett.1c01294

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  • Halogen-Bonding-Donor Catalyzed Cyanosilylation of Aldehydes Reviewed

    Ueyama, K, Hayakawa, S, Nishio, K, Sawaguchi, D, Niitsuma, K, Michii, S, Tsuruoka, R, Ozawa, M, Torita, K, Morita, Y, Komatsu, T, Haraguchi, R, Fukuzawa, S

    Asian Journal of Organic Chemistry   10 ( 7 )   1742 - 1747   2021.7

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:Wiley  

    DOI: 10.1002/ajoc.202100184

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    Other Link: https://onlinelibrary.wiley.com/doi/full-xml/10.1002/ajoc.202100184

  • Acid-Mediated Sulfonylthiolation of Arenes via Selective Activation of SS-Morpholino Dithiosulfonate Reviewed

    Kazuya Kanemoto, Koudai Furuhashi, Yoshitsugu Morita, Teruyuki Komatsu, Shin-ichi Fukuzawa

    Organic Letters   23   1582 - 1587   2021.1

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:American Chemical Society  

    DOI: 10.1021/acs.orglett.9b00875

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  • Planar-chiral ferrocene-based triazolylidene copper complexes: synthesis, characterization, and catalysis in asymmetric borylation of α,β-unsaturated ester Reviewed

    Ryosuke Haraguchi, Tatsuro Yamazaki, Koki Torita, Tatsuki Ito, Shin-ichi Fukuzawa

    Dalton Transactions   49   17578 - 17583   2020.11

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:Royal Chemical Society  

    DOI: 10.1039/D0DT03213A

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  • Lewis acid–base synergistic catalysis of cationic halogen-bonding-donors with nucleophilic counter anions Reviewed

    Koki Torita, Ryosuke Haraguchi, Yoshitsugu Morita, Satoshi Kemmochi, Teruyuki Komatsu, Shin-ichi Fukuzawa

    Chemical Communications   56   9715 - 9718   2020.7

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:Royal Society of Chemistry  

    DOI: 10.1039/D0CC04013D

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  • Copper-catalyzed Asymmetric 1,3-Dipolar Cycloaddition of Iminoesters to Unsaturated Sultones Reviewed

    Shohei Furuya, Kazuya Kanemoto, Shin-ichi Fukuzawa

    The Journal of Organic Chemistry   2020.5

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    Publishing type:Research paper (scientific journal)   Publisher:American Chemical Society (ACS)  

    DOI: 10.1021/acs.joc.0c01023

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  • クリックケミストリーによる 1,2,3−トリアゾール置換インジゴ前駆体の合成 Reviewed

    山崎達郎, 浅野陽佑, 古橋昴大, 原口良介, 所裕一郎, 福澤信一

    中央大学理工学研究所論文集   24   29 - 32   2019.3

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    Language:Japanese   Publishing type:Research paper (bulletin of university, research institution)   Publisher:中央大学  

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  • Copper-catalyzed Regio- and Diastereoselective 1,3-Dipolar Cycloaddition Reactions of Glycine Imino Esters with 1-Propene-1,3-sultone Reviewed

    Shohei Furuya, Shuma Kato, Kazuya Kanemoto, Shin-ichi Fukuzawa

    Eur. J. Org. Chem.   2019 ( 28 )   4561 - 4565   2019

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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1002/ejoc.201900738

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  • Silver-Catalyzed Diastereo- and Enantioselective Michael Addition and 1,3-Dipolar Cycloaddition Reactions of Imino Esters to 3-Methyl-4-nitro-5-styrylisoxazoles Reviewed

    Kato, S. Suzuki, Y. Suzuki, K. Haraguchi, R. Fukuzawa

    J. Org. Chem.   83 ( 22 )   13965 - 13972   2018.11

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:ACS  

    DOI: 10.1021/acs.joc.8b02309

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  • Synthesis of Ferrocene-Fused Pyrans through Alkynoxy-Directed C-H Activation/Cyclization Reviewed

    Takashi Mitsui, Yuichiro Tokoro, Ryosuke Haraguchi, Kengo Sugita, Masato Harada, Shin-ichi Fukuzawa, Yasunori Minami, Tamejiro Hiyama

    Bulletin of the Chemical Society of Japan   91 ( 5 )   839-845   2018.2

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:The Chemical Society of Japan  

    DOI: 10.1246/bcsj.20170415

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  • Intra- and intermolecular interaction of anthracene moieties in 7,8-disilabicyclo 3.3.0 octadienyl-bridged bisanthracenes Reviewed

    Tokoro, Y. Ohtsuka, N. Fukuzawa, S. I, Oyama, T

    Rsc Advances   8 ( 44 )   25177 - 25180   2018

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:RSC  

    DOI: 10.1039/c8ra05293j

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  • Twisted Polycyclic Aromatic Systems Prepared by Annulation of Bis(arylethynyl) arenes with Biphenylboronic Acids Reviewed

    Yuichiro Tokoro, Anna Oishi, Shin-ichi Fukuzawa

    CHEMISTRY-A EUROPEAN JOURNAL   22 ( 39 )   13908 - 13915   2016.9

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:WILEY-V C H VERLAG GMBH  

    Twisted polycyclic aromatic hydrocarbons (PAHs) were prepared by the successive rhodium-catalyzed annulation and dehydrogenative cyclization of bis(arylethynyl) arenes with di-tert-butylbiphenyl-2-ylboronic acid. The molecular structures of the PAHs were determined by single-crystal XRD analysis. The PAHs showed up to four fjord regions, and the twisting angle was 46.78. The nonplanarity (NP) and harmonic oscillator model of aromaticity (HOMA) were calculated by using the structural data obtained from XRD analysis. The PAHs derived from dialkynyl naphthalenes showed low planarity and HOMA of the central ring. The optical properties of the PAHs were investigated by UV/Vis absorption and fluorescence spectroscopy analyses. The absorption and emission maxima of the PAHs with a larger planar region appeared at a longer wavelength. DFT calculations support that the absorption band at lambda approximate to 450 nm can be mainly attributed to the HOMO-LUMO transition.

    DOI: 10.1002/chem.201602474

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  • Bifunctional AgOAc/ThioClickFerrophos catalyzed asymmetric 1,3-dipolar cycloaddition reaction of azomethine ylides to nitroalkenes Reviewed

    Midori Kimura, Yukiko Matsuda, Akihiro Koizumi, Chihiro Tokumitsu, Yuichiro Tokoro, Shin-ichi Fukuzawa

    TETRAHEDRON   72 ( 21 )   2666 - 2670   2016.5

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:PERGAMON-ELSEVIER SCIENCE LTD  

    AgOAc/ThioClickFerrophos (TCF) complex catalyzed the 1,3-dipolar cycloaddition of azomethine ylides (glycine imino ester) to nitroalkenes. The corresponding endo-cycloadducts (88:12-98:2 endo/exo) were afforded in good yields with high enantioselectivities, up to 98% ee, without addition of external amine. AgOAc/TCF works as a bifunctional (Lewis acid and base) catalyst. (C) 2015 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tet.2015.08.002

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  • Synthesis and Structure of N-Hetero-ortho-phenylene Hexamers Containing 2,3-Substituted Pyridine Moieties Reviewed

    Yuichiro Tokoro, Nobuhiko Ohtsuka, Ayumi Toh, Shin-ichi Fukuzawa

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY   ( 35 )   7666 - 7669   2015.12

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:WILEY-V C H VERLAG GMBH  

    N-Hetero-ortho-phenylene hexamers with two 2,3-substituted pyridine moieties (i.e., 1a-c) were prepared by palladium-catalyzed homocoupling with pyridine-directed C-H cleavage as the key step. The conformations of the resulting hexamers in solution and in the solid state were investigated by computational methods, X-ray analysis, and H-1 NMR spectroscopy. Calculations at the SCS-MP2/def2-TZVPP//B97-D3(bj)/def2-SVP level suggested that helical folding of 1a as the pyridine moieties are stacked is thermally more stable than the equivalent folding in the unsubstituted ortho-phenylene hexamer. The conformations of single crystals of 1 were consistent with the optimized structures obtained by DFT calculations. Except for rotation of the terminal phenyl groups, only one set of signals corresponding to a helical conformation was observed by analysis of 1 by H-1 NMR spectroscopy in CDCl3 solution.

    DOI: 10.1002/ejoc.201501270

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  • Synthesis and Structures of N-Hetero-ortho-Phenylene Hexamers Containing 2,3-Substituted Pyridine Moieties Reviewed

    Yuichiro Tokoro, Nobuhiko Ohtsuka, Ayumi Toh, Shin-ichi Fukuzawa

    European Journal of Organic Chemistry   ( 35 )   7666-7669   2015.11

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    DOI: 10.1002/ejoc.201501270

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  • Synthesis of Silaphenalenes by Ruthenium-Catalyzed Annulation between 1-Naphthylsilanes and Internal Alkynes through C-H Bond Cleavage Reviewed

    Yuichiro Tokoro, Kengo Sugita, Shin-ichi Fukuzawa

    Chemistry - A European Journal   21   13229-13232   2015.7

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    DOI: 10.1002/chem.201502746

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  • Silver-catalyzed asymmetric Michael addition of azomethine ylide to arylidene diphosphonates using ThioClickFerrophos ligand Reviewed

    Midori Kimura, Atsuo Tada, Yuichiro Tokoro, Shin-ichi Fukuzawa

    TETRAHEDRON LETTERS   56 ( 17 )   2251 - 2253   2015.4

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:PERGAMON-ELSEVIER SCIENCE LTD  

    Silver/ThioClickFerrophos (Ag(I)/TCF) catalyzed the asymmetric Michael addition of an azomethine ylide to arylidene diphosphonates to give syn adducts as the major diastereomers in good yields with high enantiomeric excesses. (C) 2015 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2015.03.024

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  • Development of Nickel-Catalyzed Three-Component Reactions via C-H or C-C Bond Activation Reviewed

    Kenichi Ogata, Shin-ichi Fukuzawa

    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN   70 ( 1 )   2 - 10   2012.1

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    Language:Japanese   Publishing type:Research paper (scientific journal)   Publisher:SOC SYNTHETIC ORGANIC CHEM JPN  

    The studies on nickel (0) -catalyzed three-component reactions via C-H and C-C bond activation were described. Highly regio- and stereoselective cross-trimerization of alkynes proceeded to give the corresponding 1,3-diene-5-yne by combination of triisopropylsilylacetylene and identical or distinct two alkynes via selective terminal C-H bond activation of triisopropylsilylacetylene in the presence of Ni(cod)(2)/phosphine catalyst. The methodology could be also extended toward the three-component reaction among two alkynes and a norbornene to give the 1,5-enyne. On the other hand, our interest also focused on three-component reductive coupling reaction between ring-strained cyclic alkene, aryl aldehyde and silane. Using methylenecyclopropane, reductive coupling reaction with aryl aldehyde and triisopropylsilane proceeded to yield silylated allylic alcohols via C-C bond cleavage of methylenecyclopropane ring in the presence of Ni(cod)(2)/NHC catalyst. We also found an unprecedented three-component reductive coupling via aromatic C-H bond activation of aryl aldehyde at the ortho position by combination with norbornene and triisopropylsilane leading to silylated indanol using Ni(cod)(2)NHC catalyst.

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  • Nickel-Catalyzed Three-Component Coupling between Aryl Aldehydes, Norbornenes, and Silanes Leading to Indanols through Aromatic C-H Bond Activation of Aryl Aldehydes Reviewed

    Kenichi Ogata, Yuka Atsuumi, Daisuke Shimada, Shin-ichi Fukuzawa

    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   50 ( 26 )   5896 - 5899   2011

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:WILEY-BLACKWELL  

    DOI: 10.1002/anie.201101468

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  • Synthesis of Dichlorobis(1,4-dimesityl-1H-1,2,3-triazol-5-ylidene)palladium [PdCl2(TMes)(2)] and Its Application to Suzuki-Miyaura Coupling Reaction Reviewed

    Tatsuhito Nakamura, Kenichi Ogata, Shin-ichi Fukuzawa

    CHEMISTRY LETTERS   39 ( 9 )   920 - 922   2010.9

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:CHEMICAL SOC JAPAN  

    The palladium complex bearing a novel NHC-ligand derived from 1,4-dimesityl-1,2,3-tirazole was prepared. The complex catalyzed the Suzuki-Miyaura coupling reaction with aryl chloride successfully to give biaryls in excellent yields, particularly very effective for the sterically hindered reaction between o-substituted arylchlorides and o-substituted phenylboronic acids.

    DOI: 10.1246/cl.2010.920

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  • Synthesis of Novel Ferrocenyl-Based P,S Ligands (ThioClickFerrophos) and Their Use in Pd-Catalyzed Asymmetric Allylic Substitutions Reviewed

    Minoru Kato, Tatsuhito Nakamura, Kenichi Ogata, Shin-ichi Fukuzawa

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY   ( 30 )   5232 - 5238   2009.10

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:WILEY-V C H VERLAG GMBH  

    A series of P,S ligands (ThioChckFerrophos) based on a triazoleferrocenylethyl backbone were synthesized in a four-step sequence by click chemistry methodology. The new P,S ligands were applied in allylic alkylations, etherifications, and animations of 1,3-diphenylprop-2-enyl acetate catalyzed by Pd complexes. These reactions proceeded smoothly to give products in good yields and with good enantioselectivities of up to 90 % ee. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

    DOI: 10.1002/ejoc.200900766

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  • Modular synthesis of the ClickFerrophos ligand family and their use in rhodium- and ruthenium-catalyzed asymmetric hydrogenation Reviewed

    Hiroshi Oki, Ichiro Oura, Tatsuhito Nakamura, Kenichi Ogata, Shin-ichi Fukuzawa

    TETRAHEDRON-ASYMMETRY   20 ( 18 )   2185 - 2191   2009.9

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:PERGAMON-ELSEVIER SCIENCE LTD  

    A series of diphosphine ClickFerrophos ligands (CF), based on a triazoleferrocene backbone, was synthesized in a four-step sequence via click chemistry methodology. In addition to the four previously synthesized ligands CF1, CF4, CF7 and CF10, six novel CF ligands CF2-3 and CF5-8 were prepared. Hydiogenation reactions of alkenes and ketones were significantly improved upon by using CF ligands as rhodium- or ruthenium-complexes in which the % ee values can be optimized by choosing the appropriate CF ligand depending on the substrate. (C) 2009 Elsevier Ltd All rights reserved

    DOI: 10.1016/j.tetasy.2009.09.004

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  • Copper-catalyzed direct thiolation of benzoxazole with diaryl disulfides and aryl thiols Reviewed

    Fukuzawa Shin-ichi, Shimizu Eiji, Atsuumi Yuka, Haga Masatake, Ogata Kenichi

    TETRAHEDRON LETTERS   50 ( 20 )   2374 - 2376   2009.5

  • Copper-ClickFerrophos-Complex-Catalyzed Enantioselective Reductive Aldol Reaction Reviewed

    Minoru Kato, Hiroshi Oki, Kenichi Ogata, Shin-ichi Fukuzawa

    SYNLETT   ( 8 )   1299 - 1302   2009.5

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:GEORG THIEME VERLAG KG  

    We have prepared several ClickFerrophos families and tested for the Cu(I)-catalyzed asymmetric reductive aldol reaction of ketones and aldehydes with an acrylic ester in the presence of phenylsilane. The Cu(I)-ClickFerrophos complex is efficient for the reaction of ketones with methyl acrylate to afford the erythro adducts both highly diastereo- and enantioselectively; the diastereomeric ratio of erythro/threo is improved when compared to the analogous Taniaphos.

    DOI: 10.1055/s-0029-1216724

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  • Nickel-Catalyzed Highly Regio- and Stereoselective Cross-Trimerization between Triisopropylsilylacetylene and Internal Alkynes Leading to 1,3-Diene-5-ynes Reviewed

    Kenichi Ogata, Hiroyuki Murayama, Jun Sugasawa, Noriyuki Suzuki, Shin-ichi Fukuzawa

    Journal of the American Chemical Society   131 ( 9 )   3176 - 3177   2009.3

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    The first highly selective 1:2 cross-trimerization between triisopropylsilylacetylene and 2 equiv of internal alkynes, leading to 1,3-diene-5-yne compounds, was achieved using the Ni(cod)2/PnPr3 catalyst. Various symmetrical and asymmetrical internal alkynes could be used for the cross-trimerization reaction with high regio- and stereoselectivity.

    DOI: 10.1021/ja900146u

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  • COPPER(I)-CATALYZED DIRECT ARYLATION OF 1,4-DISUBSTITUTED 1,2,3-TRIAZOLES WITH ARYL IODIDES Reviewed

    Fukuzawa Shin-ichi, Shimizu Eiji, Ogata Kenichi

    HETEROCYCLES   78 ( 3 )   645 - 655   2009.3

  • Divalent Samarium Triflate Mediated Stereoselective Pinacol Coupling of Planar Chiral Phosphanyl and Phosphoryl Ferrocenecarbaldehyde Reviewed

    Shin-ichi Fukuzawa, Ichiro Oura, Kenta Shimizu, Minoru Kato, Ken-ichi Ogata

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY   ( 5 )   716 - 720   2009.2

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:WILEY-V C H VERLAG GMBH  

    The pinacol coupling reaction of (Rp)-2-diphenylphosphanyl ferrocenecarbaldehyde (1) was smoothly mediated by divalent samarium triflate to give (R,R)-diol 2a predominantly, whereas the use of samarium(II) iodide resulted in low selectivity as described in the previous literature. In contrast, the coupling reaction of (Rp)-2-diphenylphosphoryl ferrocenecarbaldehyde (3) with Sm(OTf)(2) gave the (S,S)-diol as the major isomer, which was the opposite stereochemistry of that obtained in the reaction with 1. The rhodium complexes of diphosphanes 2a were good catalysts for the asymmetric hydrogenation of alpha-acetamidocinnamic acid, and the product was obtained quantitatively with up to 92% ee. (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

    DOI: 10.1002/ejoc.200801138

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  • Highly Chemoselective Nickel-Catalyzed Three-Component Cross-Trimerization of Three Distinct Alkynes Leading to 1,3-Dien-5-ynes Reviewed

    Kenichi Ogata, Jun Sugasawa, Shin-ichi Fukuzawa

    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   48 ( 33 )   6078 - 6080   2009

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:WILEY-V C H VERLAG GMBH  

    DOI: 10.1002/anie.200902099

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  • Phosphine-dependent selective cross-dimerization between terminal alkylacetylene and silylacetylene by Iridium(I) guanidinate complex-phosphine system Reviewed

    Kenichi Ogata, Oji Oka, Akinori Toyoda, Noriyuki Suzuki, Shin-ichi Fukuzawa

    SYNLETT   ( 17 )   2663 - 2666   2008.10

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:Georg Thieme Verlag  

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  • トリメタホスフィマト配位子を有するルテニウム、ロジウム、イリジウム錯体の構造と性質 Reviewed

    上村聡, 飯田琢也, 金尾啓一郎, 野川千種, 田辺資明, 大石克嘉, 福澤信一, 石井洋一

    中央大学理工学研究所論文集   11   1 - 10   2006.3

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  • シクロトリホスフェートを配位子とするタンタルおよびニオブ錯体の合成と構造 Reviewed

    上村聡, 大石克嘉, 福澤信一, 石井洋一

    中央大学理工学研究所論文集   2003 ( 9 )   43 - 50   2004.3

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  • Diastereoselective Alkylation of Chiral Formyl Ferrocences with Organometallic Reagents Leading to Enantiomerically Pure Ferrocenyl Aminoalcohols

    S.Fukuzawa, D.Tsuchiya, K.Sasamoto, K.Hirano, M.Ohtaguchi

    Application to Asymmetric Dialkylzinc Addition to Aldehydes and Synthesis of Symmetrical Chiral 1,2-Disubstituted Ferrocenes   2877 - 2883   2000.8

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    Language:English   Publisher:Eur.J.Org.Chem  

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  • SYNTHESES AND REACTIVITIES OF FERROCENYL ORGANYL TELLURIDES Reviewed

    Y NISHIBAYASHI, T CHIBA, JD SINGH, S UEMURA, S FUKUZAWA

    JOURNAL OF ORGANOMETALLIC CHEMISTRY   473 ( 1-2 )   205 - 213   1994.6

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:ELSEVIER SCIENCE SA LAUSANNE  

    Twenty new ferrocenyl organyl (alkyl, alkenyl and alkynyl) tellurides were synthesized by using diferrocenyl ditelluride and characterized spectroscopically. Cinnamyl and benzyl ferrocenyl tellurides were revealed to be air stable enough to be isolated, in sharp contrast to the corresponding air sensitive phenyl tellurides. Treatment of some alkyl ferrocenyl tellurides with 1 mol equiv of m-chloroperbenzoic acid (MCPBA) in diethyl ether at 25-degrees-C for 2 h in the presence of triethylamine or tetracyanoethylene (TCNE) afforded the corresponding alkenes in fair to good yields via telluroxide elimination. The MCPBA or air oxidation of some allylic ferrocenyl tellurides in ethanol produced the corresponding allylic alcohols via [2,3] sigmatropic rearrangement. H-1 NMR and electronic absorption spectroscopic studies revealed that donor-acceptor complexes between alkyl ferrocenyl tellurides and TCNE were produced, an improvement of telluroxide elimination in the presence of TCNE being attributed to this complex formation.

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  • Samarium Diiodide-induced reductive Cleavage of Se-Se and Te-Te bond in diphenly Diselenide and Ditelluride leading to a samarium phenylselenolate and tellurolate Reviewed

    S.Fukuzawa, Y.Niimoto, T.Fujinami, S.Sakai

    Heteroatom.chem   1990 ( 1 )   491 - 495   1990.12

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  • SAMARIUM(II) DIIODIDE INDUCED SYNTHESIS OF ALLYLIC PHENYL SELENIDES FROM ALLYLIC ACETATES AND DIPHENYL DISELENIDE IN THE PRESENCE OF PALLADIUM CATALYST Reviewed

    S FUKUZAWA, T FUJINAMI, S SAKAI

    CHEMISTRY LETTERS   ( 6 )   927 - 930   1990.6

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  • A New Type Surface - active Ovsanotvansitim Metal Conplex Reviewed

    S.Sakai

    J. Chem. Soc., Chem. Commun.   663 - 664   1988.4

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  • Samarium(II) di-iodide induced reductive coupling of α,(β-unsaturated esters with carbonyl compounds leading to a facile synthesis of γ-lactone Reviewed

    Shin-Ichi Fukuzawa, Akira Nakanishi, Tatsuo Fujinami, Shizuyoshi Sakai

    Journal of the Chemical Society, Perkin Transactions 1   ( 7 )   1669 - 1675   1988

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    Samarium(II) di-iodide, which is a strong one-electron transfer reducing agent, is effective for the reductive coupling of α,β-unsaturated esters with carbonyl compounds, whereby substituted γ-lactones can easily be prepared in good to excellent yields under very mild conditions. Two mole equiv. of samarium(II) di-iodide to each mole equiv. of starting substrate always give reasonable yields. The presence of an alcohol is essential in the reaction, complex unidentified products being formed in the absence of an alcohol
    t-butyl alcohol gave more satisfactory results than methanol and ethanol. The alcohol acts as a proton donor, the use of MeOD leading to a deuteriated γ-lactone. The reaction is applicable to both aliphatic and aromatic ketones or aldehydes, whereas the electrochemical method is limited to aliphatic substrates. The diastereoselectivity is examined in the reaction of 4-t-butylcyclo-hexanone with ethyl acrylate
    an anti-isomer is produced predominantly (syn: anti = 1:9) as the result of selective axial attack. The reaction may proceed by a radical mechanism, and reaction may not involve a samarium ester homoenolate. The reaction is extended to the intramolecular reaction of an α,β-unsaturated keto ester (8-oxonon-2-enoate) leading to the ready synthesis of a bicyclic γ-lactone. © 1988, The Royal Society of Chemistry. All rights reserved.

    DOI: 10.1039/P19880001669

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  • IODINE-INDUCED FORMATION OF BICYCLO[3.3.0]OCTANE DERIVATIVES FROM 1,5-CYCLOOCTADIENE Reviewed

    S UEMURA, S FUKUZAWA, A TOSHIMITSU, M OKANO, H TEZUKA, S SAWADA

    JOURNAL OF ORGANIC CHEMISTRY   48 ( 2 )   270 - 273   1983

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Books

  • ベーシックマスター 有機化学

    清水功雄, 只野金一( Role: Joint author)

    オーム社  2011.11 

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  • Scandium and Yttrium, 'Lewis Acid Reagents

    S.Fukuzawa(Edsed. By H.Yamamoto( Role: Sole author)

    1999.1 

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  • Scandium and Yttrium, 'Lewis Acid Reagents

    Oxford University Press  1999 

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  • Encyclopedia of Reagents for Organic Synthesis (10,000) Cerium(III) Trichloride-Tim(II) Chloride pp1034-1035

    L.A.Paqurtt(edit( Role: Sole author)

    1995.12 

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  • Encyclopedia of Reagents for Organic Synthesis (10,000) Cerium(Ⅲ) Trichloride-Tim(Ⅱ) Chloride pp1034-1035

    1995 

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  • Cerium(III) Trichloride-Tin(II) Chloride,'Encyclopedia of Reagents for Organic Synthesis

    S.Fukuzawa, Eds. L. A, Paqurtte, John Wiley, New York( Role: Sole author)

    1994.1 

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  • Cerium(III) Trichloride-Tin(II) Chloride,'Encyclopedia of Reagents for Organic Synthesis

    1994 

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MISC

  • Bulky iodotriazolium tetrafluoroborates as highly active halogen-bonding-donor catalysts

    Ryosuke Haraguchi, Shun Hoshino, Munenori Sakai, Sho-go Tanazawa, Yoshitsugu Morita, Teruyuki Komatsu, Shin-ichi Fukuzawa

    Chemical Communications   54 ( 73 )   10320 - 10320   2018.8

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  • Metal Complex-Controlled Regio-, Diastero- and Enantioselective 1,3-Dipolar Cycloaddition of Azomethine Ylides with Benzo[b]thiophene Sulfones

    Masato Harada, Shuma Kato, Ryosuke Haraguchi, Shin-Ichi Fukuzawa

    Chemistry - A European Journal   24 ( 11 )   2580 - 2583   2018.2

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    The Cu(MeCN)4PF6/DTBM-Segphos complex catalyzed the highly diastereo- and enantioselective 1,3-dipolar cycloaddition of azomethine ylides with benzo[b]thiophene sulfones with the usual regiochemistry to give single isomers of the exo-cycloadducts in good yields. In contrast, the AgOAc/ThioClickFerrophos complex catalyzed the reaction with atypical regiochemistry to give the endo-cycloadducts as major products with excellent enantioselectivities. Thus, the choice of chiral metal complex enabled the regio- and stereoselective synthesis of chiral fused sulfolanes.

    DOI: 10.1002/chem.201706033

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  • Palladium-Catalyzed Formylation of Alkenylzinc Reagents with S-(4-Nitrophenyl) Thioformate

    Ryosuke Haraguchi, Sho-go Tanazawa, Naoya Tokunaga, Shin-ichi Fukuzawa

    European Journal of Organic Chemistry   2018 ( 15 )   p.1761   2018.2

  • Transition-Metal-Free Formylation of Allylzinc Reagents Leading to α‑Quaternary Aldehydes Reviewed

    Ryosuke Haraguchi, Akinori Kusakabe, Nakaba Mizutani, Shin-ichi Fukuzawa

    Org. Lett.   20   1613 - 1616   2018.1

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  • Chiral triazolylidene-Pd-PEPPSI: Synthesis, characterization, and application in asymmetric Suzuki-Miyaura cross-coupling

    Ryosuke Haraguchi, Shun Hoshino, Tatsuro Yamazaki, Shin-Ichi Fukuzawa

    Chemical Communications   54 ( 17 )   2110 - 2113   2018

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    A chiral triazolylidene-Pd-PEPPSI (PEPPSI = pyridine, enhanced, precatalyst, preparation, stabilization, initiation) complex with ferrocene-based planar chirality has been synthesized and characterized. Investigation of the electronic and steric nature of this complex revealed its powerful electron-donating ability (TEP 2044 cm-1) and high steric bulk (%Vbur = 42.2). These unique properties allow the complex to exhibit very high catalytic activity (TON = 420) for asymmetric Suzuki-Miyaura cross-coupling, providing the coupling product with good enantioselectivity (75% ee).

    DOI: 10.1039/c7cc09960f

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  • Chiral Silver Complex-Catalyzed Diastereoselective and Enantioselective Michael Addition of 1-Pyrroline-5-carboxylates to alpha-Enones

    Akihiro Koizumi, Masato Harada, Ryosuke Haraguchi, Shin-Ichi Fukuzawa

    JOURNAL OF ORGANIC CHEMISTRY   82 ( 17 )   8927 - 8932   2017.9

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    A AgOAc/ThioClickFerrophos complex-catalyzed the highly diastereo- and enantioselective reaction between 1-pyrroline-5-carboxylates (1) and acyclic alpha-enones (2) in MeOH, in the presence of DBU, to give the single isomer Michael adducts (3) in high yields (up to 99%) with excellent enantioselectivies (up to 99% ee). Subsequent reduction of the Michael adducts with sodium cyanoborohydride successfully produced the fused pyrrolizidine ester as an almost pure single stereoisomer.

    DOI: 10.1021/acs.joc.7b01335

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  • Palladium-Catalyzed Formylation of Arylzinc Reagents with S-Phenyl Thioformate

    Ryosuke Haraguchi, Sho-Go Tanazawa, Naoya Tokunaga, Shin-Ichi Fukuzawa

    Organic Letters   19 ( 7 )   1646 - 1649   2017.4

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    The first example of palladium-catalyzed direct formylation of arylzinc reagents using S-phenyl thioformate is reported. The reaction proceeded under mild conditions, allowing high functional group tolerance. In addition, the developed formylation method was used to prepare deuterated and 13C-labeled aryl aldehydes from isotope-labeled S-phenyl thioformates. Moreover, this procedure was applied to an alkenylzinc halide, affording the corresponding enal.

    DOI: 10.1021/acs.orglett.7b00447

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  • Palladium-Catalyzed Formylation of Arylzinc Reagents with S-Phenyl Thioformate

    Ryosuke Haraguchi, Sho-Go Tanazawa, Naoya Tokunaga, Shin-Ichi Fukuzawa

    Organic Letters   19 ( 7 )   1646 - 1649   2017.4

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    The first example of palladium-catalyzed direct formylation of arylzinc reagents using S-phenyl thioformate is reported. The reaction proceeded under mild conditions, allowing high functional group tolerance. In addition, the developed formylation method was used to prepare deuterated and 13C-labeled aryl aldehydes from isotope-labeled S-phenyl thioformates. Moreover, this procedure was applied to an alkenylzinc halide, affording the corresponding enal.

    DOI: 10.1021/acs.orglett.7b00447

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  • Helical Folding of Hydroxy-Substituted N-Hetero-ortho-phenylenes Directed by Intramolecular Hydrogen Bonds

    Yuichiro Tokoro, Nobuhiko Ohtsuka, Akinori Kusakabe, Shin-ichi Fukuzawa

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY   ( 16 )   2353 - 2358   2017.4

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    Derivatives of the ortho-phenylene hexamer containing pyridine moieties and hydroxy groups were prepared through Negishi cross-coupling reactions between bis(chloropyridyl)biphenyl and alkoxy-substituted arylzinc reagents. X-ray diffraction analysis revealed a closed helical folding directed by pi-pi stacking and hydrogen bonds. No broadening or coalescence of H-1 NMR peaks was observed between 213 and 313 K, which indicates the high stability of the helical folding in CDCl3 solution. DFT calculations on the rotation of a single bond in the obtained compound indicated that the intramolecular hydrogen bonds led to exceptional stabilization of the closed helical folding. Right and left helices were separated by chiral column chromatography.

    DOI: 10.1002/ejoc.201700102

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  • Silver-catalyzed diastereo- and enantioselective Michael additions of 2-oxazoline- and 2-thiazoline-4-carboxylate to nitroalkenes

    Akihiro Koizumi, Yukiko Matsuda, Ryosuke Haraguchi, Shin-ichi Fukuzawa

    TETRAHEDRON-ASYMMETRY   28 ( 3 )   428 - 432   2017.3

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    The silver/ThioClickFerrophos (a chiral ferrocenyl P,S-ligand)-catalyzed Michael additions of 2-oxazolineand thiazoline-4-carboxylate to nitroalkenes were highly anti-selective and enantioselective and produced the corresponding adducts in high yields. (C) 2017 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetasy.2017.02.001

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  • Ligand-Controlled Stereodivergent, Enantioselective Conjugate Addition of 2-Oxazoline- and 2-Thiazoline-4-carboxylate to Nitroalkene Catalyzed by Chiral Copper Complexes

    Yukiko Matsuda, Akihiro Koizumi, Ryosuke Haraguchi, Shin-ichi Fukuzawa

    JOURNAL OF ORGANIC CHEMISTRY   81 ( 17 )   7939 - 7944   2016.9

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    The copper-catalyzed asymmetric conjugate addition of 2-oxazoline- and 2-thiazoline-4-carboxylate to a nitroalkene proceeded to give either the syn or anti adduct selectively in high enantiomeric excess when an appropriate chiral ligand was used. Subsequent reduction of the nitro group followed by hydrolysis of the oxazoline ring yielded an optically active gamma-lactam of protected alpha-quatemary serine derivative.

    DOI: 10.1021/acs.joc.6b01722

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  • Copper and Silver Catalyzed Diastereo- and Enantioselective Conjugate Addition Reaction of 1-Pyrroline Esters to Nitroalkenes: Diastereoselectivity switch by Chiral Metal Complexes Reviewed

    A. Koizumi, M. Kimura, Y. Arai, Y. Tokoro, S. Fukuzawa

    J. Org. Chem.   80   10883 - 10981   2015.10

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  • Synthesis of Silaphenalenes by Ruthenium-Catalyzed Annulation between 1-Naphthylsilanes and Internal Alkynes through CH Bond Cleavage

    Yuichiro Tokoro, Kengo Sugita, Shin-ichi Fukuzawa

    CHEMISTRY-A EUROPEAN JOURNAL   21 ( 38 )   13229 - 13232   2015.9

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    Ruthenium-catalyzed annulation of 1-naphthylsilanes with internal alkynes afforded silaphenalenes through cleavage of the CH bond at the 8-position of the naphthalene. [RuH2(CO){P(p-FC6H4)(3)}(3)] efficiently catalyzed the reaction. The use of 1-naphthyldiphenylsilane as a substrate resulted in a better yield of the annulation product compared to the use of silanes with alkyl groups on the silicon atom. Internal alkynes with both aryl and alkyl groups were tolerated in this reaction.

    DOI: 10.1002/chem.201502746

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  • Synthesis of pi-Conjugated Polymers Containing Benzodipyrrole Moieties in the Main Chain through Cleavage of C-H Bonds in 1,4-Bis(acetylamino)benzene

    Yuichiro Tokoro, Hiroshi Sato, Shin-ichi Fukuzawa

    ACS MACRO LETTERS   4 ( 7 )   689 - 692   2015.7

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    Rhodium-catalyzed copolymerization between 1,4-bis(acetylamino)benzene and diynes through C-H bond cleavage afforded pi-conjugated polymers containing benzodipyrrole moieties. The polymers with substituted benzene units exhibited nearly the same absorption peaks and HOMO levels. Fluorenone and benzothiadiazole moieties can be also introduced as electron-acceptor units to the main chain by polymerization in tert-amyl alcohol and tetrahydropyran as mixed solvent, leading to absorption at longer wavelength.

    DOI: 10.1021/acsmacrolett.5b00343

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  • Synthesis of adamantyl substituted 1,2,3-triazol-5-ylidene ligands and their PEPPSI-type palladium complexes

    Takashi Mitsui, Masato Sugihara, Yuichiro Tokoro, Shin-ichi Fukuzawa

    TETRAHEDRON   71 ( 10 )   1509 - 1514   2015.3

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    PEPPSI-type Pd-complexes with the bulky mesoionic 1,2,3-triazolium carbenes (tzNHC) substituted by the adamantyl groups were prepared from 1-azidoadamantane and 1-ethynyladamantane. The X-ray analysis revealed that 1,4-diadamantyl-tzNHC complex (TAd-PEPPSI) showed longer Pd-C bond length than 1-adamantyl-4-phenyl-tzNHC complex (TAdPh-PEPPSI) and 1,4-diphenyl-tzNHC complex (TPh-PEPPSI). These complexes were applied to Hiyama coupling reaction between aryl bromides and phenyltrimethoxysilane. TAd-PEPPSI rapidly initiates the reaction, and TAdPh-PEPPSI gave good product yields. (C) 2015 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tet.2015.01.040

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  • Synthesis of 7-azabicyclo[2.2.1]heptane-1-carboxylate via silver/ThioClickFerrophos-catalyzed asymmetric 1,3-dipolar cycloaddition of dihydropyrrole ester with N-substituted maleimide

    Atsuo Tada, Sayo Watanabe, Midori Kimura, Yuichiro Tokoro, Shin-ichi Fukuzawa

    TETRAHEDRON LETTERS   55 ( 45 )   6224 - 6226   2014.11

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    The AgOAc/ThioClickFerrophos-complex catalyzed the 1,3-dipolar cycloaddition of 3,4-dihydropyrrole-2-carboxylates, a precursor of cyclic azomethine ylides, with N-substituted maleimide to give the exo-cycloadducts, that is, 7-azabicyclo[2.2.1]heptane-1-carboxylates, as the major product in moderate yields with a high enantiomeric excess (up to 86% ee) under the optimized conditions. Michael adducts were produced as a minor product. (C) 2014 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2014.09.070

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  • Palladium/ClickFerrophos-Catalyzed Asymmetric Domino Allylstannylation-Heck Reaction of o-Formylaryl Triflate

    Atsuo Tada, Yuichiro Tokoro, Shin-ichi Fukuzawa

    JOURNAL OF ORGANIC CHEMISTRY   79 ( 17 )   7905 - 7909   2014.9

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    Asymmetric domino allylstannylation-Heck reaction of o-formylaryl triflates was successively catalyzed by Pd/ClickFerrophos to give the 3-methylene-indan-1-ols in good yields with good to excellent enantioselectivities. The benefit of the reaction is that the starting o-formylaryl triflates are prepared from easily accessible salicylaldehyde derivatives, and the variation of the product, chiral 3-methylene-indan-1-ols, can be expanded. The reaction with 4-substituted substrates gave the corresponding 3-methylene-indan-1-ols in good yields with high enantioselectivities, whereas the reaction with 5- and 6-substituted substrates occasionally afforded the corresponding Stille coupling product in significant amounts along with the desired 3-methylene-indan-1-ols.

    DOI: 10.1021/jo5010247

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  • Bifunctional AgOAc/ThioClickFerrophos complex-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides with aryl- and alkylidene malonates

    Sayo Watanabe, Atsuo Tada, Yuichiro Tokoro, Shin-ichi Fukuzawa

    TETRAHEDRON LETTERS   55 ( 7 )   1306 - 1309   2014.2

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    AgOAc/ThioClickFerrophos complex-catalyzed 1,3-dipolar cycloaddition of glycine imino ester, the precursor of azomethine ylide, with aryl- and alkylidene malonates afforded the corresponding exo-cycloadducts, that is, proline ester derivatives in high yields with high enantiomeric excess (up to 99% ee). The reactions proceeded smoothly under base-free conditions demonstrating the bifunctional catalysis of the silver complex. (C) 2014 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2013.12.101

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  • Silver/ThioClickFerrophos Complex as an Effective Catalyst for Asymmetric Conjugate Addition of Glycine Imino Ester to Unsaturated Malonates and alpha-Enones

    Takashi Konno, Sayo Watanabe, Tatsuki Takahashi, Yuichiro Tokoro, Shin-ichi Fukuzawa

    ORGANIC LETTERS   15 ( 17 )   4418 - 4421   2013.9

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    The AgOAc/ThioClickFerrophos complex effectively catalyzed the conjugate addition of glycine imino esters to arylidene and alkylidene malonates, furnishing the corresponding adducts in good yields with high enantioselectivities, in the presence or absence of an external base. The complex also catalyzed conjugate addition to alpha-enones in the presence of 1,4-diazabicyclo[2.2.2]octane with high enantioselectivity, with formation of a small amount of cycloadducts.

    DOI: 10.1021/ol4019584

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  • N-heterocyclic carbene copper(I) complex-catalyzed direct C-H thiolation of benzothiazoles

    Hiroshi Inomata, Ayumi Toh, Takashi Mitsui, Shin-Ichi Fukuzawa

    Tetrahedron Letters   54 ( 35 )   4729 - 4731   2013.8

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    N-heterocyclic carbene (NHC) copper(I) complexes based on imidazol-2-ylidene and 1,2,3-triazol-5-ylidene catalyzed the direct C-H thiolation of benzothiazoles and benzoxazoles with aryl and alkyl thiols to give 2-aryl and 2-alkylthiobenzothiazoles in moderate-to-good yields. The NHC copper(I) complex [(IPr)CuI] was the most effective catalyst for the reaction among the NHC-Cu(I) complexes examined in this study. © 2013 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2013.06.104

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  • 2-Ethynylpyridine-Promoted Rapid Copper(I) Chloride Catalyzed Azide-Alkyne Cycloaddition Reaction in Water

    Hidekatsu Hiroki, Kenichi Ogata, Shin-ichi Fukuzawa

    SYNLETT   24 ( 7 )   843 - 846   2013.4

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    The copper(I) chloride catalyzed reaction of azides with alkynes in water at room temperature was promoted by the addition of a catalytic amount of 2-ethynylpyridine, affording the corresponding 1,4-disubstituted 1,2,3-triazoles in good yields after a specific reaction time. The catalytic system could be successfully applied to electron-rich, electron-poor, and sterically crowded substrates. A study of the additive effect of pyridine derivatives revealed that alkynyl and 2-pyridyl groups were essential for activating the copper catalyst.

    DOI: 10.1055/s-0032-1318488

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  • Nickel-Catalyzed Ring-Opening Alkylative Coupling of Enone with Methylenecyclopropane in the Presence of Triethylborane

    Kenichi Ogata, Daisuke Shimada, Shouichi Furuya, Shin-ichi Fukuzawa

    ORGANIC LETTERS   15 ( 6 )   1182 - 1185   2013.3

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    Nickel-catalyzed alkylative coupling of an enone or enal with methylenecyclopropane in the presence of triethylborane was achieved via stereospecific proximal C-C bond cleavage of methylenecyclopropane. With the use of methylenecyclopropane possessing an acyclic alkyl substituent, this reaction was also accompanied by the beta-hydrogen elimination.

    DOI: 10.1021/ol303548x

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  • 1,2,3-トリアゾールイリデンカルベンパラジウムπーアリル錯体を用いるケトンの直接的αーアリール化反応と溝呂木ーHeck反応 Reviewed

    寺島貴大, 猪俣さゆり, 緒方賢一, 福澤信一

    中央大学理工学研究所論文集   18 ( 18 )   1 - 7   2013.3

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  • Position-selective intramolecular aromatic C-H bond activation of 1,2,3-triazol-5-ylidene (tzNHC) ligands in (p-cymene)ruthenium(ii) complexes

    Kenichi Ogata, Sayuri Inomata, Shin-Ichi Fukuzawa

    Dalton Transactions   42 ( 7 )   2362 - 2365   2013.2

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    A series of 1,2,3-triazol-5-ylidene (tzNHC) complexes of a (p-cymene)ruthenium system was synthesized. The reactivity of the N-bonded and C-bonded aryl groups in the tzNHC ligand was found to be significantly different with respect to intramolecular aromatic C-H bond activation. © 2013 The Royal Society of Chemistry.

    DOI: 10.1039/c2dt32368k

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  • Silver/ThioClickFerrophos-Catalyzed Enantioselective Conjugate Addition and Cycloaddition of Glycine Imino Ester with Nitroalkenes

    Kazumi Imae, Takashi Konno, Kenichi Ogata, Shin-ichi Fukuzawa

    ORGANIC LETTERS   14 ( 17 )   4410 - 4413   2012.9

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    We applied the combination of AgOAc with ThioClickFerrophos, the chiral ferrocenyl triazole-based P,S-ligand, to the reaction of glycine imino ester with nitroalkenes. The conjugate addition of the imino methyl ester preferentially produced anti-alpha-imino-gamma-nitrobutyrates in good yields with high enantioselectivities (ee) of up to 99% at -25 degrees C in THF in the presence of triethylamine. Meanwhile, the pyrrolidine cycloadducts were obtained as major products in good yields with high enantioselectivities (up to 96% ee) using tert-butyl imino ester in the absence of triethylamine at room temperature.

    DOI: 10.1021/ol301916t

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  • Direct C-H Carboxylation with Carbon Dioxide Using 1,2,3-Triazol-5-ylidene Copper(I) Complexes

    Hiroshi Inomata, Kenichi Ogata, Shin-ichi Fukuzawa, Zhaomin Hou

    ORGANIC LETTERS   14 ( 15 )   3986 - 3989   2012.8

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    1,2,3-Triazol-5-ylidene copper(I) complexes (tzNHC-Cu) efficiently catalyzed the direct C-H carboxylation of benzoxazole and benzothiazole derivatives with CO2 to give the corresponding esters in excellent yields after treatment with alkyl iodide. The tzNHC copper(I) complex, i.e., [(TPr)CuCl], worked somewhat more effectively than the corresponding imidazol-2-ylidene copper(I) complex [(IPr)CuCl] to give the carboxylation product in higher yields.

    DOI: 10.1021/ol301760n

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  • Stereochemistry of Substitution of the alpha-Dimethylamino Group by Dialkylzinc in Chiral Benzylferrocene

    Tatsuki Takahashi, Takashi Konno, Kenichi Ogata, Shin-ichi Fukuzawa

    JOURNAL OF ORGANIC CHEMISTRY   77 ( 15 )   6638 - 6642   2012.8

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    The stereochemistry of the substitution of the alpha-dimethylamino group by dimethylzinc in the presence of acetyl chloride in the chiral benzylferrocene backbone was examined. The reaction with the benzylferrocene bearing an o-bromo substituent at both ferrocene and the phenyl ring proceeded with inversion of configuration, while the reaction with the benzylferrocene bearing an o-bromo substituent at either ferrocene or the phenyl ring proceeded with retention of configuration.

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  • Rhodium-Catalyzed Three-Component Reaction between Silylacetylene and Two Ketenes Leading to 1,3-Enynes Bearing a Carboxylic Ester Group via Double Insertion of Ketenes

    Kenichi Ogata, Itsuki Ohashi, Shin-ichi Fukuzawa

    ORGANIC LETTERS   14 ( 16 )   4214 - 4217   2012.8

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    The first cross-reaction between a terminal silylacetylene and two ketene molecules leading to 1,3-enynes bearing a carboxylic ester group via double insertion of ketenes is achieved using a cationic rhodium complex catalyst. This reaction is applicable for various symmetrical and unsymmetrical ketenes with good stereoselectivities.

    DOI: 10.1021/ol301897h

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  • Nickel-Catalyzed Regio- and Stereoselective Reductive Coupling between Methylenecyclopropanes, Aldehydes, and Triethylborane with Retention of the Cyclopropane Ring

    Kenichi Ogata, Daisuke Shimada, Shin-ichi Fukuzawa

    CHEMISTRY-A EUROPEAN JOURNAL   18 ( 20 )   6142 - 6146   2012.5

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    DOI: 10.1002/chem.201200271

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  • Rhodium-Catalyzed Enantioselective Hydrogenation of Unsaturated Phosphonates by ClickFerrophos Ligands

    Takashi Konno, Kenta Shimizu, Kenichi Ogata, Shin-ichi Fukuzawa

    JOURNAL OF ORGANIC CHEMISTRY   77 ( 7 )   3318 - 3324   2012.4

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    Newly developed ClickFerrophos II ligands were applied in the hydrogenation of alpha,beta-unsaturated phosphonates. The use of a rhodium/ClickFerrophos II catalyst was examined in the hydrogenation of fimctionalized alpha,beta-unsaturated phosphonates and was revealed to be effective for beta-alkyl-beta-aryl or beta-dialkyl phosphonates, (Z)-beta-enolester phosphonates, and alpha-phenylethenyl phosphonates, producing the corresponding chiral phosphonates in good yields with high enantioselectivities (up to 96% ee).

    DOI: 10.1021/jo300129m

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  • Rhodium-Catalyzed Enantioselective Hydrogenation of Unsaturated Phosphonates by ClickFerrophos Ligands

    Takashi Konno, Kenta Shimizu, Kenichi Ogata, Shin-ichi Fukuzawa

    JOURNAL OF ORGANIC CHEMISTRY   77 ( 7 )   3318 - 3324   2012.4

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    Newly developed ClickFerrophos II ligands were applied in the hydrogenation of alpha,beta-unsaturated phosphonates. The use of a rhodium/ClickFerrophos II catalyst was examined in the hydrogenation of fimctionalized alpha,beta-unsaturated phosphonates and was revealed to be effective for beta-alkyl-beta-aryl or beta-dialkyl phosphonates, (Z)-beta-enolester phosphonates, and alpha-phenylethenyl phosphonates, producing the corresponding chiral phosphonates in good yields with high enantioselectivities (up to 96% ee).

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  • Synthetic, Structural, and Catalytic Studies of Well-Defined Allyl 1,2,3-Triazol-5-ylidene (tzNHC) Palladium Complexes

    Takahiro Terashima, Sayuri Inomata, Kenichi Ogata, Shin-ichi Fukuzawa

    EUROPEAN JOURNAL OF INORGANIC CHEMISTRY   ( 9 )   1387 - 1393   2012.3

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    A series of allyl 1,2,3-triazol-5-ylidene (tzNHC) palladium complexes was prepared, and the structures of the complexes were fully characterized by NMR and X-ray diffraction analyses. The donor properties of these ligands were evaluated by studying the vibrational spectra of their carbonyliridium complexes and their X-ray photoelectron spectra. These evaluations showed that the structures of the tzNHC palladium complexes are almost identical to those of the corresponding imidazole carbene palladium complexes, and that the tzNHC ligands have stronger donor properties than the imidazole carbene ligands. The relationship between catalytic activity and structure was examined by carrying out a room-temperature SuzukiMiyaura coupling reaction, and the cinnamylpalladium complex bearing 1,4-bis(2,6-diisopropylphenyl)-3-methyl-1,2,3-triazol-5-ylidene (TPr) was found to be the most active catalyst. (cinnamyl)(TPr)PdCl showed high activity in the room-temperature reaction performed with aryl chlorides regardless of the electronic and steric properties of the substituents, and was effective in reactions with sterically crowded arylboronic acids.

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  • Synthetic, Structural, and Catalytic Studies of Well-Defined Allyl 1,2,3-Triazol-5-ylidene (tzNHC) Palladium Complexes

    Takahiro Terashima, Sayuri Inomata, Kenichi Ogata, Shin-ichi Fukuzawa

    EUROPEAN JOURNAL OF INORGANIC CHEMISTRY   ( 9 )   1387 - 1393   2012.3

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    A series of allyl 1,2,3-triazol-5-ylidene (tzNHC) palladium complexes was prepared, and the structures of the complexes were fully characterized by NMR and X-ray diffraction analyses. The donor properties of these ligands were evaluated by studying the vibrational spectra of their carbonyliridium complexes and their X-ray photoelectron spectra. These evaluations showed that the structures of the tzNHC palladium complexes are almost identical to those of the corresponding imidazole carbene palladium complexes, and that the tzNHC ligands have stronger donor properties than the imidazole carbene ligands. The relationship between catalytic activity and structure was examined by carrying out a room-temperature SuzukiMiyaura coupling reaction, and the cinnamylpalladium complex bearing 1,4-bis(2,6-diisopropylphenyl)-3-methyl-1,2,3-triazol-5-ylidene (TPr) was found to be the most active catalyst. (cinnamyl)(TPr)PdCl showed high activity in the room-temperature reaction performed with aryl chlorides regardless of the electronic and steric properties of the substituents, and was effective in reactions with sterically crowded arylboronic acids.

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  • Nickel-catalyzed Diastereoselective Reductive Coupling Reaction of Norbornene with Aldehydes in the Presence of Triethylborane

    Kenichi Ogata, Ayumi Toh, Daisuke Shimada, Shin-ichi Fukuzawa

    CHEMISTRY LETTERS   41 ( 2 )   157 - 158   2012.2

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    Highly diastereoselective reductive coupling reaction was achieved between an aldehyde and a norbomene to afford an alcohol compound using a nickel/phosphine catalyst system in the presence of a reducing agent. The combination of a PCy3 ligand and triethylborane as the reducing agent proved effective for the reaction. A wide range of aldehydes were found to participate in the reaction with high diastereoselectivities.

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  • ニッケル触媒を用いるC-HおよびC-C結合の活性化を経る三成分カップリング反応の開発 Reviewed

    緒方賢一, 福澤信一

    有機合成化学協会誌   70 ( 1 )   2 - 10   2012.1

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  • Development of nickel-catalyzed three-component reactions via C-H or C-C bond activation

    Kenichi Ogata, Shin-Ichi Fukuzawa

    Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry   70 ( 1 )   2 - 10   2012

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    The studies on nickel(0)-catalyzed three-component reactions via C-H and C-C bond activation were described. Highly regio-and stereoselective cross-trimerization of alkynes proceeded to give the corresponding 1,3-diene-5-yne by combination of triisopropylsilylacetylene and identical or distinct two alkynes via selective terminal C-H bond activation of triisopropylsilylacetylene in the presence of Ni(cod) 2/phosphine catalyst. The methodology could be also extended toward the three-component reaction among two alkynes and a norbornene to give the 1,5-enyne. On the other hand, our interest also focused on three-component reductive coupling reaction between ring-strained cyclic alkene, aryl aldehyde and silane. Using methylenecyclopropane, reductive coupling reaction with aryl aldehyde and triisopropylsilane proceeded to yield silylated allylic alcohols via C-C bond cleavage of methylenecyclopropane ring in the presence of Ni(cod) 2/NHC catalyst. We also found an unprecedented three-component reductive coupling via aromatic C-H bond activation of aryl aldehyde at the ortho position by combination with norbornene and triisopropylsilane leading to silylated indanol using Ni(cod) 2/NHC catalyst.

    DOI: 10.5059/yukigoseikyokaishi.70.2

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  • 1,2,3-Triazol-5-ylidene-palladium complex catalyzed Mizoroki-Heck and Sonogashira coupling reactions

    Sayuri Inomata, Hidekatsu Hiroki, Takahiro Terashima, Kenichi Ogata, Shin-ichi Fukuzawa

    TETRAHEDRON   67 ( 38 )   7263 - 7267   2011.9

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    The bis-1,4-dimesityl-1,2,3-triazol-5-ylidene palladium complex (1a) successfully catalyzes the Mizoroki Heck and Sonogashira coupling reactions with aryl bromides to give the corresponding alkenes and alkynes, respectively, in good to excellent yields. In the Mizoroki-Heck reaction, electron-rich, electron-poor, and functionalized aryl bromides and alkenes are tolerated, while the substrates are limited to electron-poor aryl halides in the Sonogashira coupling reaction. The palladium complex also catalyzes cross-coupling reactions with aryl chlorides to give higher yields of products than does the bis-IMes-Pd complex analogue (2), under specific conditions. (C) 2011 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tet.2011.07.045

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  • Ag/ThioClickFerrophos-Catalyzed Enantioselective Mannich Reaction and Amination of Glycine Schiff Base

    Kazumi Imae, Kenta Shimizu, Kenichi Ogata, Shin-ichi Fukuzawa

    JOURNAL OF ORGANIC CHEMISTRY   76 ( 9 )   3604 - 3608   2011.5

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    The AgOAc/ThioClicicFerrophos complex catalyzed the asymmetric Mannich reaction of glycine Schiff base with N-tosylimines effectively to give a mixture of syn and anti adducts (syn/anti = 60/40-70/30) at high yields with high enantioselectivities (up to 98% ee). The complex also catalyzed the asymmetric amination of glycine Schiff base with di-tert-butyl azodicarboxylate with high enantioselectivity.

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  • Copper(I) 1,2,3-Triazol-5-ylidene Complexes as Efficient Catalysts for Click Reactions of Azides with Alkynes

    Tatsuhito Nakamura, Takahiro Terashima, Kenichi Ogata, Shin-ichi Fukuzawa

    ORGANIC LETTERS   13 ( 4 )   620 - 623   2011.2

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    Complexes of copper with 1,4-diphenyl, 1,4-dimesityl, and 1-(2,6-diisopropylphenyl)-4-(3,5-xylyl)-1,2,3-triazol-5-ylidene (abnormal NHC = N-heterocyclic carbene) were prepared by consecutive treatment of the corresponding azolium salts with silver oxide and copper chloride. The new CuCl(aNHC) complexes efficiently catalyzed click reactions of azides with alkynes to give 1,4-substituted 1,2,3-triazoles in excellent yields at room temperature with short reaction times. CuCl(TPh) was particularly effective for the reaction between sterically hindered azides and alkynes.

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  • Highly Chemoselective Nickel-Catalyzed Three-Component Cross-Trimerization between Two Distinct Terminal Alkynes and an Internal Alkyne

    Kenichi Ogata, Yuka Atsuumi, Shin-ichi Fukuzawa

    ORGANIC LETTERS   13 ( 1 )   122 - 125   2011.1

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    The highly chemo-, regio-, and stereoselective three-component cross-trimerization reaction between triisopropylsilylacetylene, diarylacetylene, and a terminal alkyne was achieved by Ni(cod)(2)/P(p-CF3C6H4)(3) catalyst at room temperature via selective C-H oxidative addition of the terminal silylacetylene. The reaction is applicable for various diarylacetylenes and terminal alkynes to yield the corresponding 1,3-diene-5-yne compounds.

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  • Nickel-Catalyzed Ring-Opening Three-Component Coupling of Methylenecyclopropane with Aldehydes and Silanes

    Kenichi Ogata, Yuka Atsuumi, Shin-ichi Fukuzawa

    ORGANIC LETTERS   12 ( 20 )   4536 - 4539   2010.10

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    A nickel-catalyzed three-component coupling between methylenecyclopropane, aldehydes, and silanes afforded silylated allylic alcohols that possess an alkyl substituent at the 2-position via cleavage of the proximal C-C bond of methylenecyclopropane

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  • トリアゾールカルベンパラジウム錯体の合成と鈴木ー宮浦カップリング反応への応用

    Nakamura, Tatsuhito, Ogata, Kenichi, Fukuzawa, Shin-ichi

    CHEMISTRY LETTERS   39 ( 9 )   920 - 922   2010.9

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  • Ag/ThioClickFerrophos catalyzed highly enantioselective 1,3-dipolar cycloaddition of azomethine ylides with alkenes

    Kenta Shimizu, Kenichi Ogata, Shin-ichi Fukuzawa

    TETRAHEDRON LETTERS   51 ( 38 )   5068 - 5070   2010.9

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    A silver(I)/ThioClickFerrophos complex catalyzed the endo selective asymmetric 1,3-dipolar cycloaddition reaction of methyl N-benzylideneglycinate (the source of azomethine ylides) with alpha,beta-unsaturated esters and maleimides to give the endo-2,4,5- and 2,3,4,5-substituted pyrrolidines in good yields with high enantioselectivities (up to 99% ee). The complex also effectively catalyzed the endo selective reactions with beta-nitrostyrene to give the 4-nitropyrrolidine in a high enantioselectivity. (C) 2010 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2010.07.085

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  • Highly chemoselective nickel-catalyzed three-component cross-trimerization of three distinct alkynes leading to 1,3-dien-5-ynes

    Kenichi Ogata, Yuka Atsuumi, Shin-ichi Fukuzawa

    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY   240   2010.8

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  • Highly enantioselective 1,3-dipolar addition of azomethine ylide with unsaturated ketones, esters, and amides

    Kenta Shimizu, Kenichi Ogata, Shin-ichi Fukuzawa

    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY   240   2010.8

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  • Synthesis of binuclear iridium(III) and rhodium(III) complexes bearing methylnaphthalene-linked N-heterocyclic carbenes, and application to intramolecular hydroamination

    Kenichi Ogata, Toshinori Nagaya, Shin-ichi Fukuzawa

    JOURNAL OF ORGANOMETALLIC CHEMISTRY   695 ( 12-13 )   1675 - 1681   2010.6

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    New methylnaphthalene-linked imidazolium salts 1 were synthesized through the reaction of 1,8-dibromomethylnaphthalene and N-alkylimidazole. On treatment of imidazolium salt 1 with silver oxide followed by [Cp*MCl(2)](2) (M = Ir, Rh), binuclear iridium and rhodium complexes 2 were formed. Reaction of these complexes 2 with AgPF(6) afforded Cl-bridged cationic binuclear iridium and rhodium complexes 3. X-ray crystallographic analysis of 3 revealed that the two imidazole rings of the carbene ligand are in a parallel geometry. The cationic binuclear iridium complexes 3-Ir could be applied to the intramolecular hydroamination reaction of 2-ethynylaniline to give the corresponding indole compound. (C) 2010 Elsevier B.V. All rights reserved.

    DOI: 10.1016/j.jorganchem.2010.04.006

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  • Highly Endo-Selective and Enantioselective 1,3-Dipolar Cycloaddition of Azomethine Ylide with alpha-Enones Catalyzed by a Silver(I)/ThioClickFerrophos Complex

    Ichiro Oura, Kenta Shimizu, Kenichi Ogata, Shin-ichi Fukuzawa

    ORGANIC LETTERS   12 ( 8 )   1752 - 1755   2010.4

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    A silver(I)/ThioClickFerrophos complex catalyzed the highly endo-selective asymmetric 1,3-dipolar cycloaddition reaction of methyl N-benzylideneglycinate (the source of azomethine ylides) with (E)-acyclic alpha-enones having an endolexo ratio of 90/10 to 99/1. The highly functionalized endo-4-acyl pyrrolidines were obtained in good yields with high enantioselectivities (up to 98% ee). The complex also effectively catalyzed endo-selective reactions with 2-cyclopentenone to give the endo-bicyclic pyrrolidine in high enantioselectivity.

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  • Highly Endo-Selective and Enantioselective 1,3-Dipolar Cycloaddition of Azomethine Ylide with alpha-Enones Catalyzed by a Silver(I)/ThioClickFerrophos Complex

    Ichiro Oura, Kenta Shimizu, Kenichi Ogata, Shin-ichi Fukuzawa

    ORGANIC LETTERS   12 ( 8 )   1752 - 1755   2010.4

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    A silver(I)/ThioClickFerrophos complex catalyzed the highly endo-selective asymmetric 1,3-dipolar cycloaddition reaction of methyl N-benzylideneglycinate (the source of azomethine ylides) with (E)-acyclic alpha-enones having an endolexo ratio of 90/10 to 99/1. The highly functionalized endo-4-acyl pyrrolidines were obtained in good yields with high enantioselectivities (up to 98% ee). The complex also effectively catalyzed endo-selective reactions with 2-cyclopentenone to give the endo-bicyclic pyrrolidine in high enantioselectivity.

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  • Nickel-Catalyzed Highly Chemo-, Regio-, and Stereoselective Three-Component Reaction of Norbornene with Two Alkynes

    Kenichi Ogata, Jun Sugasawa, Yuka Atsuumi, Shin-ichi Fukuzawa

    ORGANIC LETTERS   12 ( 1 )   148 - 151   2010.1

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    The first three-component reaction of norbornene with two alkynes leading to 1,5-enyne via C-H bond activation of terminal silylacetylene was achieved using a Ni(cod)(2)/phosphine catalyst. This reaction is applicable for various Internal alkynes and norbornene derivatives with high regio- and stereoselectivities.

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  • Synthesis of Novel Ferrocenyl-based P,S-Ligands (ThioClickFerrophos) and Their Use in Pd-Catalyzed Asymmetric Allylic Substitutions Reviewed

    M. Kato, T. Nakamura, K. Ogata, S. Fukuzawa

    Eur. J. Org. Chem.   5232 - 5238   2009.10

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  • クリックフェロホス配位子のモジュラー合成とロジウム,ルテニウム錯体触媒を用いる不斉水素化反応

    H. Oki, I. Oura, T. Nakamura, K. Ogata

    Tetrahedron: Asymmetry   20   2185 - 2191   2009.7

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  • 光学活性ピペリダジン-3-リン酸の不斉触媒反応への応用 Reviewed

    神山 章, 菊池 哲, 福澤信一

    中央大学理工学部論文集   14 ( 14 )   1 - 6   2008.12

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  • Highly enantioselective asymmetric 1,3-dipolar cycloaddition of azomethine ylide catalyzed by a copper(I)/ClickFerrophos complex

    Shin-ichi Fukuzawa, Hiroshi Oki

    ORGANIC LETTERS   10 ( 9 )   1747 - 1750   2008.5

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    A copper(I)/ClickFerrophos complex catalyzed the asymmetric 1,3-dipolar cycloaddition reaction of methyl N-benzylideneglycinate (the source of azomethine ylides) with vinyl sulfone to give the exo-2,4,5-trisubstituted pyrrolidine in good yield with high enantioselectivity (99% ee). The complex also effectively catalyzed reactions of other dipolarophiles such as acrylates, maleate, and maleimides to give the exo-2,4,5-, and 2,3,4,5-substituted pyrrolidine derivatives with high diastereo- and enantioselectivities.

    DOI: 10.1021/ol8003996

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  • Highly enantioselective asymmetric 1,3-dipolar cycloaddition of azomethine ylide catalyzed by a copper(I)/ClickFerrophos complex

    Shin-ichi Fukuzawa, Hiroshi Oki

    ORGANIC LETTERS   10 ( 9 )   1747 - 1750   2008.5

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    A copper(I)/ClickFerrophos complex catalyzed the asymmetric 1,3-dipolar cycloaddition reaction of methyl N-benzylideneglycinate (the source of azomethine ylides) with vinyl sulfone to give the exo-2,4,5-trisubstituted pyrrolidine in good yield with high enantioselectivity (99% ee). The complex also effectively catalyzed reactions of other dipolarophiles such as acrylates, maleate, and maleimides to give the exo-2,4,5-, and 2,3,4,5-substituted pyrrolidine derivatives with high diastereo- and enantioselectivities.

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  • Catalytic synthesis of 1,4-dihydropyridine derivatives using scandium(III) triflate

    Satoshi Kikuchi, Masahiro Iwai, Hiroyuki Murayama, Shin-Ichi Fukuzawa

    TETRAHEDRON LETTERS   49 ( 1 )   114 - 116   2008.1

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    Scandium(III) triflate smoothly catalyzed the reaction of imines with ethyl propiolate (2.5 equiv) to produce the corresponding N-substituted 1,4-dihydropyridines in good yields in toluene or BTF under reflux conditions. It also catalyzed the reaction of aniline and ethyl propiolate (3.2 equiv) to give another 1,4-dihydropyridine bearing three ester groups in moderate yield under the same conditions. (c) 2007 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2007.11.003

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  • Catalytic synthesis of 1,4-dihydropyridine derivatives using scandium(III) triflate

    Satoshi Kikuchi, Masahiro Iwai, Hiroyuki Murayama, Shin-Ichi Fukuzawa

    TETRAHEDRON LETTERS   49 ( 1 )   114 - 116   2008.1

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    Scandium(III) triflate smoothly catalyzed the reaction of imines with ethyl propiolate (2.5 equiv) to produce the corresponding N-substituted 1,4-dihydropyridines in good yields in toluene or BTF under reflux conditions. It also catalyzed the reaction of aniline and ethyl propiolate (3.2 equiv) to give another 1,4-dihydropyridine bearing three ester groups in moderate yield under the same conditions. (c) 2007 Elsevier Ltd. All rights reserved.

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  • ClickFerrophos: New chiral ferrocenyl phosphine ligands synthesized by Click Chemistry and the use of their metal complexes as catalysts for asymmetric hydrogenation and allylic substitution

    Shin-ichi Fukuzawa, Hiroshi Oki, Mitsuteru Hosaka, Jun Sugasawa, Satoshi Kikuchi

    ORGANIC LETTERS   9 ( 26 )   5557 - 5560   2007.12

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    The new ferrocenyl P,P- and P,N-ligands 5 and 6 (collectively, '' ClickFerrophos '') were readily prepared in four steps using Click Chemistry methodology, starting from the commercially available aminoferrocene 1. Rhodium and ruthenium complexes of ClickFerrophos 5 were effective catalysts for the hydrogenation of alkenes and ketones, respectively, producing products with up to 99.7% ee. The analogous palladium complex with 6 worked well for asymmetric allylic alkylation.

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  • ClickFerrophos: New chiral ferrocenyl phosphine ligands synthesized by Click Chemistry and the use of their metal complexes as catalysts for asymmetric hydrogenation and allylic substitution

    Shin-ichi Fukuzawa, Hiroshi Oki, Mitsuteru Hosaka, Jun Sugasawa, Satoshi Kikuchi

    ORGANIC LETTERS   9 ( 26 )   5557 - 5560   2007.12

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    The new ferrocenyl P,P- and P,N-ligands 5 and 6 (collectively, '' ClickFerrophos '') were readily prepared in four steps using Click Chemistry methodology, starting from the commercially available aminoferrocene 1. Rhodium and ruthenium complexes of ClickFerrophos 5 were effective catalysts for the hydrogenation of alkenes and ketones, respectively, producing products with up to 99.7% ee. The analogous palladium complex with 6 worked well for asymmetric allylic alkylation.

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  • Preparation of chiral homoannularly bridged N,P-Ferrocenyl ligands by intramolecular coupling of 1,5-dilithioferrocenes and their application in asymmetric allylic substitution reactions

    Shin-ichi Fukuzawa, Masahisa Yamamoto, Mitsuteru Hosaka, Satoshi Kikuchi

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY   2007 ( 33 )   5540 - 5545   2007.11

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    Homoannularly bridged ferrocene 6b was prepared by intramolecular coupling of 1,5-dilithioferrocene 5b mediated by Fe(acac)(3). Dilithioferrocene 5b was prepared by lithium-halogen exchange of the corresponding diiodide, which was prepared by 1,5-dilithiation of the o-TMS-blocked ferrocene and followed by trapping with iodine and removal of the TMS group. Alternatively, 5b could be readily prepared by the reaction of o-bromophenylferrocene 8 with nBuLi (> 2 equiv.). The benzene ring of 6b underwent ortho lithiation with tBuLi, and the resulting lithiated species was trapped with Ph2PCl to produce corresponding aminophosphane 7d. Arninophosphane 13, which has the phosphanyl group on the cyclopentarlienyl ring, was prepared by intramolecular coupling of 1,5-dilithiated PhPPFA 11 mediated by Fe(acac)3. New N,P ligands 7d and 13 were used in the palladium-catalyzed allylic alkylation and amination of 1,3-diphenyl-2-propenyl acetate (14), and ligand 7d was found to give good yields with enantioselectivities as high as 96 % ee.

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  • Preparation of chiral homoannularly bridged N,P-Ferrocenyl ligands by intramolecular coupling of 1,5-dilithioferrocenes and their application in asymmetric allylic substitution reactions

    Shin-ichi Fukuzawa, Masahisa Yamamoto, Mitsuteru Hosaka, Satoshi Kikuchi

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY   ( 33 )   5540 - 5545   2007.11

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    Homoannularly bridged ferrocene 6b was prepared by intramolecular coupling of 1,5-dilithioferrocene 5b mediated by Fe(acac)(3). Dilithioferrocene 5b was prepared by lithium-halogen exchange of the corresponding diiodide, which was prepared by 1,5-dilithiation of the o-TMS-blocked ferrocene and followed by trapping with iodine and removal of the TMS group. Alternatively, 5b could be readily prepared by the reaction of o-bromophenylferrocene 8 with nBuLi (> 2 equiv.). The benzene ring of 6b underwent ortho lithiation with tBuLi, and the resulting lithiated species was trapped with Ph2PCl to produce corresponding aminophosphane 7d. Arninophosphane 13, which has the phosphanyl group on the cyclopentarlienyl ring, was prepared by intramolecular coupling of 1,5-dilithiated PhPPFA 11 mediated by Fe(acac)3. New N,P ligands 7d and 13 were used in the palladium-catalyzed allylic alkylation and amination of 1,3-diphenyl-2-propenyl acetate (14), and ligand 7d was found to give good yields with enantioselectivities as high as 96 % ee.

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  • A novel and facile method for the synthesis of 2,3-disubstituted Quinolines by a three-component coupling reaction

    Satoshi Kikuchi, Masahiro Iwai, Shin-Ichi Fukuzawa

    SYNLETT   ( 17 )   2639 - 2642   2007.10

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    A Lewis acid effectively catalyzed the three-cornponent coupling reaction of an aromatic amine and aldehyde with ethyl propiolate, and the 2,3-disubstituted quinoline was regioselectively obtained in a good yield (up to 83% GC yield).

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  • A novel and facile method for the synthesis of 2,3-disubstituted Quinolines by a three-component coupling reaction

    Satoshi Kikuchi, Masahiro Iwai, Shin-Ichi Fukuzawa

    SYNLETT   ( 17 )   2639 - 2642   2007.10

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    A Lewis acid effectively catalyzed the three-cornponent coupling reaction of an aromatic amine and aldehyde with ethyl propiolate, and the 2,3-disubstituted quinoline was regioselectively obtained in a good yield (up to 83% GC yield).

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  • Copper(II) triflate as a double catalyst for the one-pot click synthesis of 1,4-disubstituted 1,2,3-triazoles from benzylic acetates

    Shin-ichi Fukuzawa, Eiji Shimizu, Satoshi Kikuchi

    SYNLETT   ( 15 )   2436 - 2438   2007.9

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    Copper(II) triflate doubly catalyzed the substitution of benzylic acetates by TMSN3 and the subsequent 1,3-dipolar addition with an alkyne in one pot. This procedure afforded the preparation of 1,4-disubstituted 1,2,3-triazoles in good yields starting from the easily accessible acetates without isolating an organic azide using a single catalyst.

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  • Copper(II) triflate as a double catalyst for the one-pot click synthesis of 1,4-disubstituted 1,2,3-triazoles from benzylic acetates

    Shin-ichi Fukuzawa, Eiji Shimizu, Satoshi Kikuchi

    SYNLETT   ( 15 )   2436 - 2438   2007.9

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    Copper(II) triflate doubly catalyzed the substitution of benzylic acetates by TMSN3 and the subsequent 1,3-dipolar addition with an alkyne in one pot. This procedure afforded the preparation of 1,4-disubstituted 1,2,3-triazoles in good yields starting from the easily accessible acetates without isolating an organic azide using a single catalyst.

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  • キラルビナフチル基を有する新規光学活性フェロセンの合成と変換反応 Reviewed

    山本真久, 菊地 哲, 石井洋一, 福澤信一

    中央大学理工学研究所論文集   12 ( 12 )   99 - 105   2007.3

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  • Unexpected 1,5-dilithiation of chiral o-TMS blocked (dimethylamino) phenylmethylferrocene: An alternative approach to chiral ferrocenyl 1,5-diphosphanes

    Shin-Ichi Fukuzawa, Masahisa Yamamoto, Satoshi Kikuchi

    Journal of Organic Chemistry   72 ( 4 )   1514 - 1517   2007.2

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    (Chemical Equation Presented) The 1,5-dilithiation of o-TMS blocked (dimethylamino)phenylmethylferrocene 4 unexpectedly occurred even though one equimolar amount of t-BuLi was used and the 1,5-dilithiated ferrocene 6 was trapped by iodine followed by removal of the TMS group to give the 1,5-diiodoferrocene 11 in a reasonable yield. The 1,5-diiodoferrocene 11 was converted into the diastereomer of Taniaphos 12 by sequential dilithiation and trapping with Ph2PCl. The rhodium and copper complex of 12 catalyzed well the asymmetric allylic alkylation with a Grignard reagent and hydrogenation with the α-acetamidocinnamic acid ester, respectively, with high enantioselectivities. The methoxy 1,5-diphosphane 14, of which the enantiomer is known as a good ligand for the rhodium-catalyzed asymmetric hydrogenation, was obtained by the inversive substitution of the dimethylamino group of 11 by NaOMe and subsequent dilithiation and trapping with Ph2PCl. © 2007 American Chemical Society.

    DOI: 10.1021/jo062210l

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  • Unexpected 1,5-dilithiation of chiral o-TMS blocked (dimethylamino)phenylmethylferrocene: An alternative approach to chiral ferrocenyl 1,5-diphosphanes

    Shin-ichi Fukuzawa, Masahisa Yamamoto, Satoshi Kikuchi

    JOURNAL OF ORGANIC CHEMISTRY   72 ( 4 )   1514 - 1517   2007.2

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    The 1,5-dilithiation of o-TMS blocked (dimethylamino)phenylmethylferrocene 4 unexpectedly occurred even though one equimolar amount of t-BuLi was used and the 1,5-dilithiated ferrocene 6 was trapped by iodine followed by removal of the TMS group to give the 1,5-diiodoferrocene 11 in a reasonable yield. The 1,5-diiodoferrocene 11 was converted into the diastereomer of Taniaphos 12 by sequential dilithiation and trapping with Ph2PCl. The rhodium and copper complex of 12 catalyzed well the asymmetric allylic alkylation with a Grignard reagent and hydrogenation with the alpha-acetamidocinnamic acid ester, respectively, with high enantioselectivities. The methoxy 1,5-diphosphane 14, of which the enantiomer is known as a good ligand for the rhodium-catalyzed asymmetric hydrogenation, was obtained by the inversive substitution of the dimethylamino group of 11 by NaOMe and subsequent dilithiation and trapping with Ph2PCl.

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  • Prepation of New Chiral Ferrocenyl Phosphine and Amine Ligands and Their Application to Asymmetric Synthesis

    17th International Symposium on Fine Chemistry and Polymers   46 ( 5 )   569   2007

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  • Three-component Coupling of Amine, Aldehyde, Ethyl Propiolate Catalyzed by Lewis Acid

    14th International Symposium on Organometallic Chemistry directed towards Organic Synthesis   2007

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  • Preparation of New Chiral Triazoleferrocenyl Ligands using Click Chemistry

    14th International Symposium on Organometallic Chemistry directed towards Organic Synthesis   2007

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  • Palladium-catalyzed coupling reaction of diaryl dichalcogenide with aryl bromide leading to the synthesis of unsymmetrical aryl chalcogenide

    Shin-ichi Fukuzawa, Daisuke Tanihara, Satoshi Kikuchi

    SYNLETT   ( 13 )   2145 - 2147   2006.8

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    An efficient cross-coupling reaction of diphenyl disulfide or diselenide with substituted aryl bromides using PdCl2(dppf) and zinc has been developed. This method gave functionalized unsymmetrical aryl sulfides and selenides in good to excellent yields under neutral conditions.

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  • Palladium-catalyzed coupling reaction of diaryl dichalcogenide with aryl bromide leading to the synthesis of unsymmetrical aryl chalcogenide

    Shin-ichi Fukuzawa, Daisuke Tanihara, Satoshi Kikuchi

    SYNLETT   ( 13 )   2145 - 2147   2006.8

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    An efficient cross-coupling reaction of diphenyl disulfide or diselenide with substituted aryl bromides using PdCl2(dppf) and zinc has been developed. This method gave functionalized unsymmetrical aryl sulfides and selenides in good to excellent yields under neutral conditions.

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  • Asymmetric conjugate addition of O-benzylhydroxylamine to alpha,beta-unsaturated 3-acyloxazolidin-2-ones catalyzed by Sc(OTf)(3)/i-Pr-pybox complex

    Satoshi Kikuchi, Hiroaki Sato, Shin-ichi Fukuzawa

    SYNLETT   ( 7 )   1023 - 1026   2006.5

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    The asymmetric conjugate addition of 0-benzylhydroxylamine to alpha,beta-unsaturated 3-acyloxazolidin-2-ones was smoothly catalyzed by the Sc(OTf)(3)/2,6-bis[(S)-4-isopropyloxazolin-2-yl]pyridine (i-Pr-pybox) complex in the presence of MS 4 A to give the corresponding beta-amino acids in good conversions with high enantioselectivities (up to 91% ee).

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  • Asymmetric conjugate addition of O-benzylhydroxylamine to alpha,beta-unsaturated 3-acyloxazolidin-2-ones catalyzed by Sc(OTf)(3)/i-Pr-pybox complex

    Satoshi Kikuchi, Hiroaki Sato, Shin-ichi Fukuzawa

    SYNLETT   ( 7 )   1023 - 1026   2006.5

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    The asymmetric conjugate addition of 0-benzylhydroxylamine to alpha,beta-unsaturated 3-acyloxazolidin-2-ones was smoothly catalyzed by the Sc(OTf)(3)/2,6-bis[(S)-4-isopropyloxazolin-2-yl]pyridine (i-Pr-pybox) complex in the presence of MS 4 A to give the corresponding beta-amino acids in good conversions with high enantioselectivities (up to 91% ee).

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  • Preparation of new, optically active 1,2-ferrocenyldiamine ligands and their application to ruthenium-catalyzed asymmetric transfer hydrogenation of ketones

    S Fukuzawa, T Suzuki

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY   ( 4 )   1012 - 1016   2006.2

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    The treatment of (R,R)-1,2-bis(1-acetoxy-1-phenylmethyl)ferrocene (1) with azidotrimethylsilane in CH2Cl2 in the presence of a catalytic amount of a Lewis acid such as Cu(OTf)(2) or Sc(OTf)(3), at -40 degrees C for 24 h, gives a mixture of two diastereomeric ferrocenyl diazides 4 and 5 in an 80:20 ratio. The major isomer (R,R)-4 is formed with retention of configuration at both benzylic chiral centers whereas the minor isomer meso- (R, S) -5 is formed with inversion of configuration at one of the two chiral centers. After a shorter reaction time (12 h), the (R,R)-ferrocenylazido acetate 6 was isolated as a single diastereomer, which gave 4 and 5 under the same conditions with almost the same ratio as with the longer reaction time. These results show that the first step of the reaction is the substitution, with retention of configuration, of the exo acetate of 1 by means of an iron-assisted ionization, i.e., neighboring-group participation, then the endo acetate is replaced by the azide ion with retention or inversion of configuration to give 4 or 5, respectively. The optically active complex 4 could be converted into the corresponding ferrocenyldiamme 2 by reduction with LiAIH(4), and its ditosylamide 8a and di-acetamide 8b were isolated as stable compounds. The ferrocenyldiamine and both diamides were used as ligands in the ruthenium-catalyzed asymmetric transfer hydrogenation of aryl ketones, and the complex with 2 gave 1-arylethanols in good yields with up to 75% ee. (c) Wiley-VCH Verlag GmbH & Co.

    DOI: 10.1002/ejoc.200500660

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  • Preparation of new, optically active 1,2-ferrocenyldiamine ligands and their application to ruthenium-catalyzed asymmetric transfer hydrogenation of ketones

    S Fukuzawa, T Suzuki

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY   2006 ( 4 )   1012 - 1016   2006.2

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    The treatment of (R,R)-1,2-bis(1-acetoxy-1-phenylmethyl)ferrocene (1) with azidotrimethylsilane in CH2Cl2 in the presence of a catalytic amount of a Lewis acid such as Cu(OTf)(2) or Sc(OTf)(3), at -40 degrees C for 24 h, gives a mixture of two diastereomeric ferrocenyl diazides 4 and 5 in an 80:20 ratio. The major isomer (R,R)-4 is formed with retention of configuration at both benzylic chiral centers whereas the minor isomer meso- (R, S) -5 is formed with inversion of configuration at one of the two chiral centers. After a shorter reaction time (12 h), the (R,R)-ferrocenylazido acetate 6 was isolated as a single diastereomer, which gave 4 and 5 under the same conditions with almost the same ratio as with the longer reaction time. These results show that the first step of the reaction is the substitution, with retention of configuration, of the exo acetate of 1 by means of an iron-assisted ionization, i.e., neighboring-group participation, then the endo acetate is replaced by the azide ion with retention or inversion of configuration to give 4 or 5, respectively. The optically active complex 4 could be converted into the corresponding ferrocenyldiamme 2 by reduction with LiAIH(4), and its ditosylamide 8a and di-acetamide 8b were isolated as stable compounds. The ferrocenyldiamine and both diamides were used as ligands in the ruthenium-catalyzed asymmetric transfer hydrogenation of aryl ketones, and the complex with 2 gave 1-arylethanols in good yields with up to 75% ee. (c) Wiley-VCH Verlag GmbH & Co.

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  • Preparation and structures of chiral mono and bis ortho-aminoalkyl-substituted 1,1 '-trichalcogena[3]ferrocenophanes

    S Fukuzawa, D Wachi

    HETEROATOM CHEMISTRY   17 ( 2 )   118 - 124   2006

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    We prepared a series of mono and bis ortho-aminoalkyl-substituted chiral trichalcogena[3]-ferrocenophanes by dilithiation of mono- and bis-aminoferrocenes and subsequent reaction with sulfur and selenium in moderate yields. The X-ray crystallographic analyses of triselena[3]ferrocenophanes revealed that the bridge selenium atom was directed toward to the ortho-substituent (endo). In the bis-type ferrocenophanes, bridge inversion was not detected by H-1 NMR because they would be homomeric. (c) 2006 Wiley Periodicals, Inc.

    DOI: 10.1002/hc.20189

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  • Preparation of New Chiral Ferrocenyl Diamines and Their Related Compounds and Their Application to Asymmetric Synthesis

    XXIIth Inthernational Symposium on Organometallic Chemsitry   2006

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  • Preparation and structures of chiral mono and bis ortho-aminoalkyl-substituted 1,1 '-trichalcogena[3]ferrocenophanes

    S Fukuzawa, D Wachi

    HETEROATOM CHEMISTRY   17 ( 2 )   118 - 124   2006

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    We prepared a series of mono and bis ortho-aminoalkyl-substituted chiral trichalcogena[3]-ferrocenophanes by dilithiation of mono- and bis-aminoferrocenes and subsequent reaction with sulfur and selenium in moderate yields. The X-ray crystallographic analyses of triselena[3]ferrocenophanes revealed that the bridge selenium atom was directed toward to the ortho-substituent (endo). In the bis-type ferrocenophanes, bridge inversion was not detected by H-1 NMR because they would be homomeric. (c) 2006 Wiley Periodicals, Inc.

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  • Stereoselective pinacol coupling of chiral formylferrocene using divalent samarium triflate: Preparation of a new chiral bisferrocenyl oxazoline ligand and its application to asymmetric Diels-Alder reactions

    S Fukuzawa, Y Yahara, A Kamiyama, M Hara, S Kikuchi

    ORGANIC LETTERS   7 ( 26 )   5809 - 5812   2005.12

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    The pinacol coupling reaction of planar chiral ortho-oxazoline-substituted formylferrocene was smoothly mediated by Sml(2) or Sm(OTf)(3) to give the (R,R) isomer selectivity (up to 76% diastereomeric excess). The combination of Yb(OTf)(3) and the (R,R)-ferrocenyl diol was revealed to be a good catalyst for the asymmetric Diels-Alder reaction of 3-acyloxazolidinone with cyclopentadiene, and the endo adduct was produced in up to 80% enantiomeric excess.

    DOI: 10.1021/ol0523291

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  • Stereoselective pinacol coupling of chiral formylferrocene using divalent samarium triflate: Preparation of a new chiral bisferrocenyl oxazoline ligand and its application to asymmetric Diels-Alder reactions

    S Fukuzawa, Y Yahara, A Kamiyama, M Hara, S Kikuchi

    ORGANIC LETTERS   7 ( 26 )   5809 - 5812   2005.12

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    The pinacol coupling reaction of planar chiral ortho-oxazoline-substituted formylferrocene was smoothly mediated by Sml(2) or Sm(OTf)(3) to give the (R,R) isomer selectivity (up to 76% diastereomeric excess). The combination of Yb(OTf)(3) and the (R,R)-ferrocenyl diol was revealed to be a good catalyst for the asymmetric Diels-Alder reaction of 3-acyloxazolidinone with cyclopentadiene, and the endo adduct was produced in up to 80% enantiomeric excess.

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  • Pinacol Coupling Reaction of Planner Chiral Formylferrocene by Samarium(II) Complexes

    KAMIYAMA Akira

    46   226 - 227   2005.5

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  • Preparation of Chiral 1,4-Ferrocenyl Diazide and Diamide and Their Derivatives

    Recent Advances in catalysis 2005   2005

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  • Preparation of Chiral ortho-Substituted Diferrocenyl 1,2-Diol and Its Application to Asymmetric Cycloadditions

    PACIFICHEM 2005   2005

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  • A facile synthesis of a New Chiral Ferrocene based on Binaphtyl Chiral Auxiliary

    PACIFIHEM 2005   2005

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  • Preparation of New Chiral Bisferrocenyl Oxazoline by Pinacol Coupling of Chiral Formylferrocenes and Its Application to Asymmetric Synthesis

    Recent Advances in Catalysis   2005

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  • Regioselective aminolysis and hydrolysis of chiral 1,4-ferrocenyl diacetate

    S Fukuzawa, D Wachi, T Suzuki, S Itoh

    JOURNAL OF ORGANIC CHEMISTRY   69 ( 15 )   4991 - 4996   2004.7

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    The treatment of (1-R,4R)-1,2-bis(phenylmethyl)ferrocenyl diacetate 2a with aqueous ammonium in THF/MeOH at room temperature for 18 h gave the single diastereomer of the (1R,4R,Sp)-1,2-acetoamido alcohol 4a with retention of the configuration. This result showed that the aminolysis occurred regioselectively at one side of the two acetates. Similarly, hydrolysis of the diacetate 2a at room temperature for 18 h occurred regio- and stereoselectively to give the optically active half-ester 10 in a good yield. The ease of the substitution may depend on the geometry of the two stereogenic centers. Only one of the acetoxy groups is suitably aligned for ionization (exo to the ferrocenyl group) to proceed efficiently; the aminolysis takes place smoothly by iron-assisted ionization, i.e., neighboring group participation. The leaving group on the second acetoxy group is not suitably aligned (endo, to the ferrocenyl group) and also cannot undergo a conformational change for it to adopt the appropriate orientation for ionization to occur. This reaction is the first case of substitution in a chiral molecule in which a conformational difference between two leaving groups happened to affect the rate of aminolysis and hydrolysis at two stereogenic centers.

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  • Regioselective aminolysis and hydrolysis of chiral 1,4-ferrocenyl diacetate

    S Fukuzawa, D Wachi, T Suzuki, S Itoh

    JOURNAL OF ORGANIC CHEMISTRY   69 ( 15 )   4991 - 4996   2004.7

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    The treatment of (1-R,4R)-1,2-bis(phenylmethyl)ferrocenyl diacetate 2a with aqueous ammonium in THF/MeOH at room temperature for 18 h gave the single diastereomer of the (1R,4R,Sp)-1,2-acetoamido alcohol 4a with retention of the configuration. This result showed that the aminolysis occurred regioselectively at one side of the two acetates. Similarly, hydrolysis of the diacetate 2a at room temperature for 18 h occurred regio- and stereoselectively to give the optically active half-ester 10 in a good yield. The ease of the substitution may depend on the geometry of the two stereogenic centers. Only one of the acetoxy groups is suitably aligned for ionization (exo to the ferrocenyl group) to proceed efficiently; the aminolysis takes place smoothly by iron-assisted ionization, i.e., neighboring group participation. The leaving group on the second acetoxy group is not suitably aligned (endo, to the ferrocenyl group) and also cannot undergo a conformational change for it to adopt the appropriate orientation for ionization to occur. This reaction is the first case of substitution in a chiral molecule in which a conformational difference between two leaving groups happened to affect the rate of aminolysis and hydrolysis at two stereogenic centers.

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  • Regioselective aminolysis and hydrolysis of chiral 1,4-ferrocenyl diacetate

    S Fukuzawa, D Wachi, T Suzuki, S Itoh

    JOURNAL OF ORGANIC CHEMISTRY   69 ( 15 )   4991 - 4996   2004.7

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    The treatment of (1-R,4R)-1,2-bis(phenylmethyl)ferrocenyl diacetate 2a with aqueous ammonium in THF/MeOH at room temperature for 18 h gave the single diastereomer of the (1R,4R,Sp)-1,2-acetoamido alcohol 4a with retention of the configuration. This result showed that the aminolysis occurred regioselectively at one side of the two acetates. Similarly, hydrolysis of the diacetate 2a at room temperature for 18 h occurred regio- and stereoselectively to give the optically active half-ester 10 in a good yield. The ease of the substitution may depend on the geometry of the two stereogenic centers. Only one of the acetoxy groups is suitably aligned for ionization (exo to the ferrocenyl group) to proceed efficiently; the aminolysis takes place smoothly by iron-assisted ionization, i.e., neighboring group participation. The leaving group on the second acetoxy group is not suitably aligned (endo, to the ferrocenyl group) and also cannot undergo a conformational change for it to adopt the appropriate orientation for ionization to occur. This reaction is the first case of substitution in a chiral molecule in which a conformational difference between two leaving groups happened to affect the rate of aminolysis and hydrolysis at two stereogenic centers.

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  • Reduction of carbonyl compounds by lanthanide metal/2-propanol: In-situ generation of samarium isopropyloxide for stereoselective Meerwein-Ponndorf-Verley reduction

    S Fukuzawa, N Nakano, T Saitoh

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY   ( 13 )   2863 - 2867   2004.6

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    The reduction of ketones and aldehydes with lanthanide metals (La, Ce, Sm, Yb) and a catalytic amount of iodine (5 mol %) in iPrOH proceeded smoothly to produce the corresponding alcohols as the major products in good yield, while in THF, methanol, and ethanol the pinacols were mainly produced. The yields of alcohols were improved most effectively by the use of Sm metal, the amount of pinacol produced thus being minimized. The actual reducing agent may be samarium isopropyloxide, which mediates the Meerwein-Ponndorf-Verley-type hydride-transfer reaction, since the reaction can be carried out catalytically with respect to samarium. The stereoselectivities of the reductions of the 2- and 4-substituted cyclohexanones with Sm/iPrOH were higher than those achieved with SmI2/iPrOH or Sm/H2O. The asymmetric reduction of acetophenone could be achieved to give the 1-phenylethanol in up to 95 % ee in the presence of the chiral ligand 7. (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

    DOI: 10.1002/ejoc.200400030

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  • Reduction of carbonyl compounds by lanthanide metal/2-propanol: In-situ generation of samarium isopropyloxide for stereoselective Meerwein-Ponndorf-Verley reduction

    S Fukuzawa, N Nakano, T Saitoh

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY   ( 13 )   2863 - 2867   2004.6

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    The reduction of ketones and aldehydes with lanthanide metals (La, Ce, Sm, Yb) and a catalytic amount of iodine (5 mol %) in iPrOH proceeded smoothly to produce the corresponding alcohols as the major products in good yield, while in THF, methanol, and ethanol the pinacols were mainly produced. The yields of alcohols were improved most effectively by the use of Sm metal, the amount of pinacol produced thus being minimized. The actual reducing agent may be samarium isopropyloxide, which mediates the Meerwein-Ponndorf-Verley-type hydride-transfer reaction, since the reaction can be carried out catalytically with respect to samarium. The stereoselectivities of the reductions of the 2- and 4-substituted cyclohexanones with Sm/iPrOH were higher than those achieved with SmI2/iPrOH or Sm/H2O. The asymmetric reduction of acetophenone could be achieved to give the 1-phenylethanol in up to 95 % ee in the presence of the chiral ligand 7. (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

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  • Chiral Rare Earth Complex Catalyzed Asymmetric Cycloaddition Reactions

    Rare Earth '04 in Nara JAPAN   2004

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  • Asymmetric Diels-Alder reactions in supercritical carbon dioxide catalyzed by rare earth complexes

    S Fukuzawa, K Metoki, S Esumi

    TETRAHEDRON   59 ( 52 )   10445 - 10452   2003.12

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    The rare earth(III) salt catalysed asymmetric Diels-Alder reaction of cyclopentadiene with a chiral dienophile in supercritical carbon dioxide (scCO(2)) proceeded rapidly to give the adduct with a higher diastereoselectivity than that in dichloromethane; Yb(ClO4)(3) gave the endo adduct with value up to 77% de at 40degreesC, 8 MPa. The chiral rare earth diketonate catalyzed hetero Diels-Alder reaction of the Danishefsky's diene with benzaldehyde gave a higher yield and an enantioselectivity in scCO(2) than that in dichloromethane. Scandium/pybox 8a complex catalysed asymmetric Diels-Alder reaction of 3-crotonoyl-2-oxazolidinone with cyclopentadiene in the presence of MS4A proceeded smoothly in scCO(2) to give the endo adduct 10 in a good yield with up to 88% ee. (C) 2003 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tet.2003.04.009

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  • Asymmetric Diels-Alder reactions in supercritical carbon dioxide catalyzed by rare earth complexes

    S Fukuzawa, K Metoki, S Esumi

    TETRAHEDRON   59 ( 52 )   10445 - 10452   2003.12

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    The rare earth(III) salt catalysed asymmetric Diels-Alder reaction of cyclopentadiene with a chiral dienophile in supercritical carbon dioxide (scCO(2)) proceeded rapidly to give the adduct with a higher diastereoselectivity than that in dichloromethane; Yb(ClO4)(3) gave the endo adduct with value up to 77% de at 40degreesC, 8 MPa. The chiral rare earth diketonate catalyzed hetero Diels-Alder reaction of the Danishefsky's diene with benzaldehyde gave a higher yield and an enantioselectivity in scCO(2) than that in dichloromethane. Scandium/pybox 8a complex catalysed asymmetric Diels-Alder reaction of 3-crotonoyl-2-oxazolidinone with cyclopentadiene in the presence of MS4A proceeded smoothly in scCO(2) to give the endo adduct 10 in a good yield with up to 88% ee. (C) 2003 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tet.2003.04.009

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  • Reduction of ketimines by samarium(II) complexes. isolation and structural characterization of samarium(III) eta(1)-amine/eta(1)-ketimido and eta(2)-ketimine complexes

    ZM Hou, C Yoda, T Koizumi, M Nishiura, Y Wakatsuki, S Fukuzawa, J Takats

    ORGANOMETALLICS   22 ( 17 )   3586 - 3592   2003.8

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    The reaction of (C5Me5)(2)Sm(THF)(2) with 2 equiv of benzophenone imine (Ph2C=NH) in THF at room temperature gave the samarocene(III) amine/ketimido complex (C5Me5)(2)Sm(N=CPh2)(NH2CHPh2) (1) in 58% isolated yield. The use of 1 equiv of Ph2C=NH also afforded 1 as the only isolable product, albeit in a lower yield (ca. 20%). Deuterium-labeling experiments suggest that 1 is formed via hydrogen abstraction by the in-situ-generated imine radical anion species, followed by acid-base reaction between the resulting amido species and another molecule of Ph2C=NH. The reactions of 2 equiv of Sm(OAr)(2)(THF)(3) (Ar = (C6H2Bu2)-Bu-t-2,6-Me-4) with N-phenyl benzophenone imine (Ph2C=NPh) and N-phenyl fluorenone imine (C12H8C=NPh) yielded the Sm(III) eta(2)-imine-dianion/aryloxide complexes Sm(eta(2)-Ph-2-CNPh)(OAr)(THF)(3) (3, 65%) and Sm(eta(2)-C12H8CNPh)(OAr)(THF)(3) (4, 77%), respectively, together with the byproduct Sm(OAr)(3). The reaction of 1 equiv of Sm(OAr)(2)(THF)(3) with Ph2C=NPh also gave the imine-dianion complex 3, whereas an imine radical anion species was not observed. Similarly, the reactions of 2 equiv of SmtN(SiMe3)(2)}(2)(THF)(2) with Ph-2-C=NPh and C12H8C=NPh yielded the q2-imine-dianion/silylamido complexes Sm(eta(2)-(PhCNPh)-C-2){N(SiMe3)(2)}(THF)(3) (5, 87%) and Sm(eta(2)-C12H8CNPh){N(SiMe3)(2)}(THF)(3) (6, 71%), respectively. Complexes 3-6 represent the first examples of structurally characterized trivalent lanthanide eta(2)-imine complexes.

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  • Reduction of ketimines by samarium(II) complexes. isolation and structural characterization of samarium(III) eta(1)-amine/eta(1)-ketimido and eta(2)-ketimine complexes

    ZM Hou, C Yoda, T Koizumi, M Nishiura, Y Wakatsuki, S Fukuzawa, J Takats

    ORGANOMETALLICS   22 ( 17 )   3586 - 3592   2003.8

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    The reaction of (C5Me5)(2)Sm(THF)(2) with 2 equiv of benzophenone imine (Ph2C=NH) in THF at room temperature gave the samarocene(III) amine/ketimido complex (C5Me5)(2)Sm(N=CPh2)(NH2CHPh2) (1) in 58% isolated yield. The use of 1 equiv of Ph2C=NH also afforded 1 as the only isolable product, albeit in a lower yield (ca. 20%). Deuterium-labeling experiments suggest that 1 is formed via hydrogen abstraction by the in-situ-generated imine radical anion species, followed by acid-base reaction between the resulting amido species and another molecule of Ph2C=NH. The reactions of 2 equiv of Sm(OAr)(2)(THF)(3) (Ar = (C6H2Bu2)-Bu-t-2,6-Me-4) with N-phenyl benzophenone imine (Ph2C=NPh) and N-phenyl fluorenone imine (C12H8C=NPh) yielded the Sm(III) eta(2)-imine-dianion/aryloxide complexes Sm(eta(2)-Ph-2-CNPh)(OAr)(THF)(3) (3, 65%) and Sm(eta(2)-C12H8CNPh)(OAr)(THF)(3) (4, 77%), respectively, together with the byproduct Sm(OAr)(3). The reaction of 1 equiv of Sm(OAr)(2)(THF)(3) with Ph2C=NPh also gave the imine-dianion complex 3, whereas an imine radical anion species was not observed. Similarly, the reactions of 2 equiv of SmtN(SiMe3)(2)}(2)(THF)(2) with Ph-2-C=NPh and C12H8C=NPh yielded the q2-imine-dianion/silylamido complexes Sm(eta(2)-(PhCNPh)-C-2){N(SiMe3)(2)}(THF)(3) (5, 87%) and Sm(eta(2)-C12H8CNPh){N(SiMe3)(2)}(THF)(3) (6, 71%), respectively. Complexes 3-6 represent the first examples of structurally characterized trivalent lanthanide eta(2)-imine complexes.

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  • New chiral scandium(III)/bisimine and diol complexes catalyzed asymmetric Diels-Alder reaction

    S Fukuzawa, Y Komuro, N Nakano, S Obara

    TETRAHEDRON LETTERS   44 ( 18 )   3671 - 3674   2003.4

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    Several bisimine and diol-based chiral ligands were examined as scandium(Ill) triflate complexes in the asymmetric Diels-Alder reaction of cyclopentadiene (2) with 3-acryloyloxazolidin-2-one (1) in the presence of 2,6-lutidine: the scandium/salen complex was revealed to be the most effective catalyst, which afforded the endo adduct in a good yield with 85% ee. Addition of a tertiary amine, such as 2,6-lutidine, was critical to achieve high enantioselectivity; enantioselectivity was remarkably decreased in the absence of the amine. (C) 2003 Elsevier Science Ltd. All rights reserved.

    DOI: 10.1016/S0040-4039(03)00674-9

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  • New chiral scandium(III)/bisimine and diol complexes catalyzed asymmetric Diels-Alder reaction

    S Fukuzawa, Y Komuro, N Nakano, S Obara

    TETRAHEDRON LETTERS   44 ( 18 )   3671 - 3674   2003.4

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    Several bisimine and diol-based chiral ligands were examined as scandium(Ill) triflate complexes in the asymmetric Diels-Alder reaction of cyclopentadiene (2) with 3-acryloyloxazolidin-2-one (1) in the presence of 2,6-lutidine: the scandium/salen complex was revealed to be the most effective catalyst, which afforded the endo adduct in a good yield with 85% ee. Addition of a tertiary amine, such as 2,6-lutidine, was critical to achieve high enantioselectivity; enantioselectivity was remarkably decreased in the absence of the amine. (C) 2003 Elsevier Science Ltd. All rights reserved.

    DOI: 10.1016/S0040-4039(03)00674-9

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  • One-step highly diastereoselective synthesis of gamma-aminoalkyl-substituted gamma-butyrolactones by an asymmetric samarium-mediated ketyl-alkene coupling reaction

    S Fukuzawa, M Miura, T Saitoh

    JOURNAL OF ORGANIC CHEMISTRY   68 ( 5 )   2042 - 2044   2003.3

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    The samarium(II) iodide mediated reaction of N,N-dibenzyl-protected (S)-alpha-amino aldehydes with (1S,2R)-N-methylephedrinyl acrylate gave the (4R,1'S)-gamma-(aminoalkyl)-gamma-butyrolactones in good yields with high diastereoselectivities (up to 80% de); (4R,1'S)-gamma-amino-(2-phenylethyl)-gamma-butyrolactone (6a), which should be a potent precursor for gamma-secretase inhibitors, was obtained with high de value.

    DOI: 10.1021/jo020574h

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  • One-step highly diastereoselective synthesis of gamma-aminoalkyl-substituted gamma-butyrolactones by an asymmetric samarium-mediated ketyl-alkene coupling reaction

    S Fukuzawa, M Miura, T Saitoh

    JOURNAL OF ORGANIC CHEMISTRY   68 ( 5 )   2042 - 2044   2003.3

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    The samarium(II) iodide mediated reaction of N,N-dibenzyl-protected (S)-alpha-amino aldehydes with (1S,2R)-N-methylephedrinyl acrylate gave the (4R,1'S)-gamma-(aminoalkyl)-gamma-butyrolactones in good yields with high diastereoselectivities (up to 80% de); (4R,1'S)-gamma-amino-(2-phenylethyl)-gamma-butyrolactone (6a), which should be a potent precursor for gamma-secretase inhibitors, was obtained with high de value.

    DOI: 10.1021/jo020574h

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  • New synthetic methods for optically active ferrocenes and their application to asymmetric synthesis

    Shinichi Fukuzawa

    Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry   61 ( 3 )   211 - 225   2003

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    A classical route to chiral ferrocenes is optical resolution of the racemate and limited compounds have been prepared by this method. Recent successes in the synthesis of a variety of chiral ferrocenes without optical resolution now have attracted considerable attention in asymmetric synthesis. The chiral ferrocenylalcohols, -amines, -acetals, and -oxazolines can be readily prepared from achiral acyl-, formylferrocenes, and ferrocenecarboxylic acids. These substituents attached to cyclopentadienyl group of ferrocenes are strong ortho directing groups which lead to planar chiral ferrocenes with highly regioselection (&gt
    99% de). The planar chiral ferrocene can be also prepared by enantioselective lithiation of the achiral ferrocenylamide and amine with the chiral lithium reagent. C2 symmetrical 1, 1′-ferrocenediol is obtained from asymmetric reduction of 1, 1′-diacyl ferrocene and can be converted to the corresponding ferrocenediamine and -diphosphine derivatives. New planar chiral ferrocenyl phosphines and alcohols are examined in the benchmark asymmetric allylic substitution and dialkylzinc addition to an aldehyde, respectively.

    DOI: 10.5059/yukigoseikyokaishi.61.211

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  • Preparation and Transformation of Chiral 1,2-disubstituted Ferrocenes: A Chiral Ferrocene with a Better Arm

    Dalton Discussions 6: Organometallic Chemistry and Catalysis   2003

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  • Chiral Rare Earth Complex Asymmetric Diels-Alder Reaction in Supercritical Carbon Dioxide

    International Symposium on Organic Synthesis   2003

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  • Chiral Rare Earth/Bisimine Complex Catalyzed Enantioselective Carbonyl Enene Reaction and 1,3-Dipolar Reaction

    50th Symposium on Organometallic Chemsitry   2003

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  • Preparation and Transformation of Chiral 1,2-Disubstituted Ferrocenes; The Chiral Ferrocene with a Stronger Arm

    50th Symposium on Organometallic Chemsitry   2003

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  • シクリトール誘導体を不斉源として用いたエナンチオ選択的アルキル化反応 Reviewed

    秋山隆彦, 堀口尚史, 小川昭弥, 福沢信一

    中央大学理工学研究所論文集   8 ( 8 )   59 - 62   2002.12

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  • Efficient preparation of C-2-symmetrical chiral ferrocenyl diols by catalytic enantioselective reduction of diacylferrocenes

    H Sato, H Watanabe, Y Ohtsuka, T Ikeno, S Fukuzawa, T Yamada

    ORGANIC LETTERS   4 ( 19 )   3313 - 3316   2002.9

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    Enantioselective borohydride reduction, catalyed by the optically active beta-ketoiminato cobalt(II) complex, was successfully applied to the 1,1'-dialkanoyl- and 1,1'-dibenzoylferrocenes to afford the corresponding C-2-symmetrical chiral ferrocenyl diols with high diastereoselectivity and excellent enantioselectivity.

    DOI: 10.1021/ol0266018

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  • Efficient preparation of C-2-symmetrical chiral ferrocenyl diols by catalytic enantioselective reduction of diacylferrocenes

    H Sato, H Watanabe, Y Ohtsuka, T Ikeno, S Fukuzawa, T Yamada

    ORGANIC LETTERS   4 ( 19 )   3313 - 3316   2002.9

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    Enantioselective borohydride reduction, catalyed by the optically active beta-ketoiminato cobalt(II) complex, was successfully applied to the 1,1'-dialkanoyl- and 1,1'-dibenzoylferrocenes to afford the corresponding C-2-symmetrical chiral ferrocenyl diols with high diastereoselectivity and excellent enantioselectivity.

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  • Copper(II)-catalyzed kinetic resolution of (±)-2-arylpropionic acids with chiral N-trimethylsilyloxazolidin-2-one

    Shin-Ichi Fukuzawa, Yoshiaki Chino, Tetsuhiro Yokoyama

    Tetrahedron Asymmetry   13 ( 15 )   1645 - 1649   2002.8

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    The reaction between (±)-2-arylpropanoyl chlorides 1 (2 equiv.) and enantiopure N-trimethylsilyloxazolidin-2-one 2 in the presence of a catalytic amount of CuCl2 in hexane affords the corresponding N-acyloxazolidin-2-one in good chemical yields (97%) with up to 50% de. © 2002 Elsevier Science Ltd. All rights reserved.

    DOI: 10.1016/S0957-4166(02)00409-3

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  • Copper(II)-catalyzed kinetic resolution of (+/-)-2-arylpropionic acids with chiral N-trimethylsilyloxazolidin-2-one

    S Fukuzawa, Y Chino, T Yokoyama

    TETRAHEDRON-ASYMMETRY   13 ( 15 )   1645 - 1649   2002.8

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    The reaction between (+/-)-2-arylpropanoyl chlorides 1 (2 equiv.) and enantiopure N-trimethylsilyoxazolidin-2-one 2 in the presence of a catalytic amount of CuCl2 in hexane affords the corresponding N-acyloxazolidin-2-one in good chemical yields (97%) with up to 50% de. (C) 2002 Elsevier Science Ltd. All rights reserved.

    DOI: 10.1016/S0957-4166(02)00409-3

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  • Optically active 1,2-bis(1-arylhydroxymethyl) ferrocene: A new, efficient chiral ligand for scandium-catalyzed asymmetric Diels-Alder reaction

    S Fukuzawa, K Fujimoto, Y Komuro, H Matsuzawa

    ORGANIC LETTERS   4 ( 5 )   707 - 709   2002.3

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    [GRAPHICS]
    The Sc(OTf)(3)/FERRODIOL (2) complex was prepared at -78degreesC in CH2Cl2 in the presence of 2,6-lutidine and MS 4A. The chiral scandium Lewis acid-catalyzed asymmetric Diels-Alder reaction of cyclopentadiene (3) with 3-acyloxazolidin-2-ones (4) effectively produced the adduct (5) in a high yield with good selectivity, i.e., endo/exo = 90:10 up to 91% ee (endo).

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  • Optically active 1,2-bis(1-arylhydroxymethyl) ferrocene: A new, efficient chiral ligand for scandium-catalyzed asymmetric Diels-Alder reaction

    S Fukuzawa, K Fujimoto, Y Komuro, H Matsuzawa

    ORGANIC LETTERS   4 ( 5 )   707 - 709   2002.3

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    [GRAPHICS]
    The Sc(OTf)(3)/FERRODIOL (2) complex was prepared at -78degreesC in CH2Cl2 in the presence of 2,6-lutidine and MS 4A. The chiral scandium Lewis acid-catalyzed asymmetric Diels-Alder reaction of cyclopentadiene (3) with 3-acyloxazolidin-2-ones (4) effectively produced the adduct (5) in a high yield with good selectivity, i.e., endo/exo = 90:10 up to 91% ee (endo).

    DOI: 10.1021/ol0171766

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  • Rare earth salt catalyzed asymmetric Diels-Alder reaction with a chiral dienophile in supercritical carbon dioxide: Enhancement effect on stereoselectivity

    SI Fukuzawa, K Metoki, Y Komuro, T Funazukuri

    SYNLETT   ( 1 )   134 - 136   2002.1

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    The rare earth(III) salt catalyzed asymmetric Diels-Alder reaction of cyclopentadiene with a chiral dienophile in super-critical carbon dioxide (scCO(2)) proceeded rapidly to give the adduct with a higher diastereoselectivity than that in dichloromethane; optimization of the CO2 density increased the de value up to 77%.

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  • Rare earth salt catalyzed asymmetric Diels-Alder reaction with a chiral dienophile in supercritical carbon dioxide: Enhancement effect on stereoselectivity

    SI Fukuzawa, K Metoki, Y Komuro, T Funazukuri

    SYNLETT   ( 1 )   134 - 136   2002.1

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    The rare earth(III) salt catalyzed asymmetric Diels-Alder reaction of cyclopentadiene with a chiral dienophile in super-critical carbon dioxide (scCO(2)) proceeded rapidly to give the adduct with a higher diastereoselectivity than that in dichloromethane; optimization of the CO2 density increased the de value up to 77%.

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  • Halogenolactamization of 2-(3-butenyl)-1,3-oxazolines to bifunctional gamma- and delta-lactams

    Terao, K, Takechi, Y, Kunishima, M, Tani, S, Ito, A, Yamasaki, C, Fukuzawa, S

    Chemistry Letters   ( 5 )   522 - 523   2002

  • Halogenolactamization of 2-(3-butenyl)-1,3-oxazolines to bifunctional gamma- and delta-lactams

    Terao, K, Takechi, Y, Kunishima, M, Tani, S, Ito, A, Yamasaki, C, Fukuzawa, S

    Chemistry Letters   ( 5 )   522 - 523   2002

  • クロロシラン共存下における低原子価サマリウム試薬によるケトン類の還元反応 Reviewed

    小川昭弥, 田中宏道, 秋山隆彦, 福沢信一

    中央大学理工学研究所論文集   7 ( 7 )   37 - 43   2001.11

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  • Diastereoselective addition of organometallics to chiral amino formyl- and acylferrocenes: Synthesis of a chiral 1,2-homo disubstituted ferrocene

    S Fukuzawa, K Fujimoto

    SYNLETT   ( 8 )   1275 - 1277   2001.8

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    The addition of Grignard reagents to the ortho-amimo-formylferrocene (4) gave the corresponding amino alcohol (5a) of which the chiral center of the newly formed alcoholic carbon had the R configuration as the major diastereomer in 26-82% de, On the other hand, the stereochemical outcome was in contrast to the dialkylzinc addition to 7, the alcoholic carbon being the S configuration. The reduction of the chiral ortho-aminobenzoylferrocenes (7, 8) with DIBAH gave the corresponding amino alcohol (5a, 9a) with the R configuration of the alcoholic carbon as single diastereomers. while the reduction with LiAlH4 produced them with the S configuration of the alcoholic carbon as major diastereomers.

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  • Diastereoselective addition of organometallics to chiral amino formyl- and acylferrocenes: Synthesis of a chiral 1,2-homo disubstituted ferrocene

    S Fukuzawa, K Fujimoto

    SYNLETT   ( 8 )   1275 - 1277   2001.8

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    The addition of Grignard reagents to the ortho-amimo-formylferrocene (4) gave the corresponding amino alcohol (5a) of which the chiral center of the newly formed alcoholic carbon had the R configuration as the major diastereomer in 26-82% de, On the other hand, the stereochemical outcome was in contrast to the dialkylzinc addition to 7, the alcoholic carbon being the S configuration. The reduction of the chiral ortho-aminobenzoylferrocenes (7, 8) with DIBAH gave the corresponding amino alcohol (5a, 9a) with the R configuration of the alcoholic carbon as single diastereomers. while the reduction with LiAlH4 produced them with the S configuration of the alcoholic carbon as major diastereomers.

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  • Diastereoselective reduction and carbon-carbon bond formation of alpha-keto esters/amides with SmI2

    S Fukuzawa, M Miura, H Matsuzawa

    TETRAHEDRON LETTERS   42 ( 25 )   4167 - 4169   2001.6

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    The stereoselective reduction of alpha -keto esters/alpha -keto amides, which have various chiral auxiliaries using SmI2, is examined. 2(S)-Methoxymethylpyrrolidine, 1,1,2(S)- and 1,1,2(R)-triphenylethanediol were found to be suitable chiral auxiliaries that produced the corresponding alpha -hydroxy ester and amide in good diastereoselectivity with satisfactory yields. Allylation, the Reformatsky-type reaction, and the ketyl-alkene coupling reaction with the 1,1,2(R)-triphenylethanediol and 2(S)-methoxymethylpyrrolidine, derivative of the alpha -keto ester/amide proceeded smoothly with high diastereoselectivity. (C) 2001 Elsevier Science Ltd. All rights reserved.

    DOI: 10.1016/S0040-4039(01)00676-1

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  • Diastereoselective reduction and carbon-carbon bond formation of alpha-keto esters/amides with SmI2

    S Fukuzawa, M Miura, H Matsuzawa

    TETRAHEDRON LETTERS   42 ( 25 )   4167 - 4169   2001.6

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    The stereoselective reduction of alpha -keto esters/alpha -keto amides, which have various chiral auxiliaries using SmI2, is examined. 2(S)-Methoxymethylpyrrolidine, 1,1,2(S)- and 1,1,2(R)-triphenylethanediol were found to be suitable chiral auxiliaries that produced the corresponding alpha -hydroxy ester and amide in good diastereoselectivity with satisfactory yields. Allylation, the Reformatsky-type reaction, and the ketyl-alkene coupling reaction with the 1,1,2(R)-triphenylethanediol and 2(S)-methoxymethylpyrrolidine, derivative of the alpha -keto ester/amide proceeded smoothly with high diastereoselectivity. (C) 2001 Elsevier Science Ltd. All rights reserved.

    DOI: 10.1016/S0040-4039(01)00676-1

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  • Scandium(III) triflate/isopropyl-pybox complex as an efficient catalyst for asymmetric Diels-Alder reaction

    S Fukuzawa, H Matsuzawa, K Metoki

    SYNLETT   ( 5 )   709 - 711   2001.5

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    The chiral scandium (III) triflate/i-Pr-pybox complex efficiently catalyzes the asymmetric Diels-Alder reaction of 1,3-dienes with acyl-1,3-oxazolidin-2-ones (1a-c) afford the corresponding adducts in good yields with up to 90% ee. The reaction can be carried out in less toxic benzotrifluoride and supercritical carbon dioxide while remaining good selectivity (65-75% ee).

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  • Scandium(III) triflate/isopropyl-pybox complex as an efficient catalyst for asymmetric Diels-Alder reaction

    S Fukuzawa, H Matsuzawa, K Metoki

    SYNLETT   ( 5 )   709 - 711   2001.5

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    The chiral scandium (III) triflate/i-Pr-pybox complex efficiently catalyzes the asymmetric Diels-Alder reaction of 1,3-dienes with acyl-1,3-oxazolidin-2-ones (1a-c) afford the corresponding adducts in good yields with up to 90% ee. The reaction can be carried out in less toxic benzotrifluoride and supercritical carbon dioxide while remaining good selectivity (65-75% ee).

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  • Samarium(II) Iodide Mediated Kinetic resolution of Chiral Ketones and Aldehydes by the Coupling Reaction with Chiral Acrylic Acid Esters

    11th Symposium on Organometallic Chemistry directed toward Organic Synthesis, P208, Taipei   2001

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  • Synthesis of Chiral 1,2-Ferrocenyldiphosphines and Their Application to Asymmetric Synthesis

    11th Symposium on Organometallic Chemistry directed toward Organic Synthesis, P208, Taipei   2001

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  • Scandium(III) Triflate/1,2-Ferrocendiol Complex Catalyzed Asymmetric Diels-Alder Reaction

    11th Symposium on Organometallic Chemistry directed toward Organic Synthesis, P208, Taipei   2001

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  • Rare Earth(II) Lewis Acid Catalysed Asymmetric Diels-Alder Reaction in Supercritical Carbon Dioxide

    11th Symposium on Organometallic Chemistry directed toward Organic Synthesis, P208, Taipei   2001

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  • Diastereoselective 1,2-addition of organometallic reagents to chiral formylferrocenes leading to enantiomerically pure ferrocenyl amino alcohols: Application to asymmetric dialkylzinc addition to aldehydes and synthesis of optically active 1,2-homodisubstituted ferrocenes

    S Fukuzawa, D Tsuchiya, K Sasamoto, K Hirano, M Ohtaguchi

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY   ( 16 )   2877 - 2883   2000.8

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    The chiral formylferrocenes 2-5 have been readily prepared in good yields by ortho-lithiation of the TMS-blocked or unblocked aminoferrocenes and subsequent reaction with DMF. The stereochemistry of the reaction of 2 with organometallic reagents has been examined. Reactions of 2 with Grignard and organolithium reagents gave the corresponding amino alcohol 6 in good yields with moderate to high diastereomeric excesses (up to 99%). When a dialkylzine was used as the nucleophile, a single diastereomer was obtained almost exclusively. This reaction may be rationalized in terms of an autocatalytic mechanism; the zinc alkoxide 7 generated in situ functions as an activator of dialkylzinc, which then adds to the formyl group. We have examined the asymmetric diethylzinc addition to benzaldehyde using formylferrocenes 2-5 or ferrocenyl amino alcohols 6a, 13 as catalysts, especially with regard to the relationship between catalytic activity and the chirality of the diastereomeric ferrocenes. Alkylation with 2, 3, and 6a gave (1R)-phenyl-1-propanol in good yields with high ee values (87-91% eel. On the other hand, reactions with 4, 5, and 13 gave the (S)-product in low yield and with low ee (38-57% eel. The low stereoselectivities can be attributed to stereochemical mismatching in the zinc alkoxides derived from 4 and 5. With aromatic, straight-chain, or branched aliphatic aldehydes, the stereoselective alkylation successfully gave the corresponding alcohols in good to high optical purities when 2 or 3 was employed as the catalyst. The optically active 1,2-ferrocenediol and -diphosphane have been prepared by means of the stereospecific substitution reaction with the amino alcohol 13 on treatment with acetic anhydride, followed by hydrolysis or substitution with diphenylphosphane.

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  • Diastereoselective 1,2-addition of organometallic reagents to chiral formylferrocenes leading to enantiomerically pure ferrocenyl amino alcohols: Application to asymmetric dialkylzinc addition to aldehydes and synthesis of optically active 1,2-homodisubstituted ferrocenes

    S Fukuzawa, D Tsuchiya, K Sasamoto, K Hirano, M Ohtaguchi

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY   ( 16 )   2877 - 2883   2000.8

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    The chiral formylferrocenes 2-5 have been readily prepared in good yields by ortho-lithiation of the TMS-blocked or unblocked aminoferrocenes and subsequent reaction with DMF. The stereochemistry of the reaction of 2 with organometallic reagents has been examined. Reactions of 2 with Grignard and organolithium reagents gave the corresponding amino alcohol 6 in good yields with moderate to high diastereomeric excesses (up to 99%). When a dialkylzine was used as the nucleophile, a single diastereomer was obtained almost exclusively. This reaction may be rationalized in terms of an autocatalytic mechanism; the zinc alkoxide 7 generated in situ functions as an activator of dialkylzinc, which then adds to the formyl group. We have examined the asymmetric diethylzinc addition to benzaldehyde using formylferrocenes 2-5 or ferrocenyl amino alcohols 6a, 13 as catalysts, especially with regard to the relationship between catalytic activity and the chirality of the diastereomeric ferrocenes. Alkylation with 2, 3, and 6a gave (1R)-phenyl-1-propanol in good yields with high ee values (87-91% eel. On the other hand, reactions with 4, 5, and 13 gave the (S)-product in low yield and with low ee (38-57% eel. The low stereoselectivities can be attributed to stereochemical mismatching in the zinc alkoxides derived from 4 and 5. With aromatic, straight-chain, or branched aliphatic aldehydes, the stereoselective alkylation successfully gave the corresponding alcohols in good to high optical purities when 2 or 3 was employed as the catalyst. The optically active 1,2-ferrocenediol and -diphosphane have been prepared by means of the stereospecific substitution reaction with the amino alcohol 13 on treatment with acetic anhydride, followed by hydrolysis or substitution with diphenylphosphane.

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  • Asymmetric Samarium-Reformatsky reaction of chiral alpha-bromoacetyl-2-oxazolidinones with aldehydes

    S Fukuzawa, H Matsuzawa, S Yoshimitsu

    JOURNAL OF ORGANIC CHEMISTRY   65 ( 6 )   1702 - 1706   2000.3

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    The samarium(II) iodide mediated asymmetric Reformatsky-type reaction of chiral 3-bromoacetyl-2-oxazolidinones with various aldehydes was studied. A series of chiral 4-substituted 2-oxazolidinones 1-3 and 5,5-disubstituted "SuperQuat" oxazolidinones 4-5 were employed as chiral auxiliaries of the alpha-bromoacetic acid: The reaction of 1 with various aldehydes gave the alpha-unbranched beta-hydroxy carboximides in good yields with high diastereomeric excess values (up to >99% de). The majority of the reaction product derived from 5,5-diphenyl SuperQuat 5 were highly crystallinity; a single recrystallization yielding a diastereomerically pure product with the other diastereomer not detectable by spectroscopic methods.' The absolute configurations of the beta-hydroxy carboximides were determined by signs of optical rotations of the corresponding known ethyl esters referring to the literature values. Hydrolytic cleavage of the appended of beta-hydroxy moieties from the auxiliary SuperQuats was readily achieved under mild conditions using lithium hydroxide; the corresponding carboxylic acids and the returned SuperQuats were obtained in good yields without any evidence of racemization. The first step of the reaction is the reduction of the alpha-bromo group to produce the samarium enolate, which adds to an aldehyde. The absolute configuration of the adduct (7i) derive from benzaldehyde was found to be R, with the samarium enolate favoring the transition state predicted from chelation control of the reagent; this is in analogy to the discussion that has been used for the corresponding titanium enolate. The stereochemistry of the reaction may be explained by incorporating the Nerz-Stormes-Thornton chair transition structure model.

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  • Asymmetric Samarium-Reformatsky reaction of chiral alpha-bromoacetyl-2-oxazolidinones with aldehydes

    S Fukuzawa, H Matsuzawa, S Yoshimitsu

    JOURNAL OF ORGANIC CHEMISTRY   65 ( 6 )   1702 - 1706   2000.3

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    The samarium(II) iodide mediated asymmetric Reformatsky-type reaction of chiral 3-bromoacetyl-2-oxazolidinones with various aldehydes was studied. A series of chiral 4-substituted 2-oxazolidinones 1-3 and 5,5-disubstituted "SuperQuat" oxazolidinones 4-5 were employed as chiral auxiliaries of the alpha-bromoacetic acid: The reaction of 1 with various aldehydes gave the alpha-unbranched beta-hydroxy carboximides in good yields with high diastereomeric excess values (up to >99% de). The majority of the reaction product derived from 5,5-diphenyl SuperQuat 5 were highly crystallinity; a single recrystallization yielding a diastereomerically pure product with the other diastereomer not detectable by spectroscopic methods.' The absolute configurations of the beta-hydroxy carboximides were determined by signs of optical rotations of the corresponding known ethyl esters referring to the literature values. Hydrolytic cleavage of the appended of beta-hydroxy moieties from the auxiliary SuperQuats was readily achieved under mild conditions using lithium hydroxide; the corresponding carboxylic acids and the returned SuperQuats were obtained in good yields without any evidence of racemization. The first step of the reaction is the reduction of the alpha-bromo group to produce the samarium enolate, which adds to an aldehyde. The absolute configuration of the adduct (7i) derive from benzaldehyde was found to be R, with the samarium enolate favoring the transition state predicted from chelation control of the reagent; this is in analogy to the discussion that has been used for the corresponding titanium enolate. The stereochemistry of the reaction may be explained by incorporating the Nerz-Stormes-Thornton chair transition structure model.

    DOI: 10.1021/jo9914317

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  • Diastereoselective Reduction snd C-C Bond Formation of Homochiral alpha-Keto Esters/Amides by Smamarium(II) Iodide

    PACIFICHEM 2000, Honolulu, USA   2000

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  • Diastereoselective Reduction snd C-C Bond Formation of Homochiral alpha-Keto Esters by Smamarium(II) Iodide

    4th International Symposium on Transition Metals in Organic Synthesis, Leeds, UK   2000

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  • Diastereoselective Alkylation and Reduction of Chiral Formyl and Acylferrocenes

    PS-172   2000

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  • Kinetic resolution of alpha-acetoxy carboxylic acids with homochiral SuperQuats

    SP Bew, SG Davies, SI Fukuzawa

    CHIRALITY   12 ( 5-6 )   483 - 487   2000

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    Preliminary investigations focused on the kinetic resolution of (+)-alpha-acetoxy mandelic carboxylic acid chloride with isopropyl SuperQuat and isopropyl Evans' homochiral auxiliaries. The addition of 2 equiv. of the acid chloride to the lithium salts of the auxiliaries (SuperQuat and Evans') at -100 degrees C in the THF afforded the corresponding N-acyl auxiliaries in high chemical yields (95% and 89%) and d.e.'s of 66% and 40%, respectively. Using the same mandelic acid chloride but incorporating SuperQuat aux iliaries derived from (S)-phenylglycine and (S)-phenylalanine yielded the corresponding N-acyl SuperQuats in 86% and 90% and d.e.'s of 66% and 30%, respectively. Substituting the phenyl group within the cr-acetoxy mandelic acid chloride for a n-butyl, tert-butyl and cyclohexyl group changed the d.e. significantly when kinetically resolved with isopropyl SuperQuat. The yields were all similar, i.e., similar to 90% but the d.e.'s varied considerably, with values of 20%, 50%, and 82%, respectively. Attempted kinetic resolution of alpha-methoxy-phenylacetyl chloride using the lithium salt of isopropyl SuperQuat revealed a diasteroselectivity of 45%, significantly lower than that obtained with the corresponding alpha-acetoxy carboxylic acid chlorides. (C) 2000 Wiley-Liss, Inc.

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  • Kinetic resolution of alpha-acetoxy carboxylic acids with homochiral SuperQuats

    SP Bew, SG Davies, SI Fukuzawa

    CHIRALITY   12 ( 5-6 )   483 - 487   2000

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    Preliminary investigations focused on the kinetic resolution of (+)-alpha-acetoxy mandelic carboxylic acid chloride with isopropyl SuperQuat and isopropyl Evans' homochiral auxiliaries. The addition of 2 equiv. of the acid chloride to the lithium salts of the auxiliaries (SuperQuat and Evans') at -100 degrees C in the THF afforded the corresponding N-acyl auxiliaries in high chemical yields (95% and 89%) and d.e.'s of 66% and 40%, respectively. Using the same mandelic acid chloride but incorporating SuperQuat aux iliaries derived from (S)-phenylglycine and (S)-phenylalanine yielded the corresponding N-acyl SuperQuats in 86% and 90% and d.e.'s of 66% and 30%, respectively. Substituting the phenyl group within the cr-acetoxy mandelic acid chloride for a n-butyl, tert-butyl and cyclohexyl group changed the d.e. significantly when kinetically resolved with isopropyl SuperQuat. The yields were all similar, i.e., similar to 90% but the d.e.'s varied considerably, with values of 20%, 50%, and 82%, respectively. Attempted kinetic resolution of alpha-methoxy-phenylacetyl chloride using the lithium salt of isopropyl SuperQuat revealed a diasteroselectivity of 45%, significantly lower than that obtained with the corresponding alpha-acetoxy carboxylic acid chlorides. (C) 2000 Wiley-Liss, Inc.

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  • 二価のサマリウム錯体を用いる不斉有機合成反応

    希土類   ( 35 )   33 - 39   1999.11

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  • Cyclodextrin complexes of bisepoxide and of alpha,omega-diamine in several molar ratios. Preparation and characterization in the solid state

    Yamaguchi, I, H Ishii, K Osakada, T Yamamoto, S Fukuzawa

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   72 ( 7 )   1541 - 1545   1999.7

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    Addition of 1,4-butanediol diglycidyl ether (glycidyl = 2,3-epoxypropyl) to aqueous solutions of alpha-cyclodextrin (CD) leads to separation of the 2 : 1 complex from the solution. The C-13 CP/MAS NMR spectrum of the complex indicates the presence of diastereomeric oxirane groups formed via the complexation. 1,4-Butanediol diglycidyl ether forms the 1 : 1 or 2 : 2 complex with gamma-CD similarly from the aqueous reactions of the two compounds. 2,2-Dimethyltrimethylene glycol diglycidyl ether also forms water-insoluble host-guest complexes with (alpha-CD (2 : 1) and with gamma-CD (1 : 1 or 2 : 2). Poly(propylene glycol diglycidyl ether) with an M-n of 640 reacts with beta-CD to give the 1 : 4 complex. Poly(tetrahydrofuran) terminated with NH2 groups at both ends also forms the 1 :4 complexes both with alpha-CD and with gamma-CD.

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  • Cyclodextrin complexes of bisepoxide and of α,ω-diamine in several molar ratios. Preparation and characterization in the solid state

    Isao Yamaguchi, Hidetake Ishii, Kohtaro Osakada, Takakazu Yamamoto, Shin-Ichi Fukuzawa

    Bulletin of the Chemical Society of Japan   72 ( 7 )   1541 - 1545   1999.7

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    Addition of 1,4-butanediol diglycidyl ether (glycidyl = 2,3- epoxypropyl) to aqueous solutions of α-cyclodextrin (CD) leads to separation of the 2:1 complex from the solution. The 13C CP/MAS NMR spectrum of the complex indicates the presence of diastereomeric oxirane groups formed via the complexation. 1,4-Butanediol diglycidyl ether forms the 1:1 or 2:2 complex with γ-CD similarly from the aqueous reactions of the two compounds. 2,2-Dimethyltrimethylene glycol diglycidyl ether also forms water-insoluble host-guest complexes with α-CD (2:1) and with γ-CD (1:1 or 2:2). Poly(propylene glycol diglycidyl ether) with an M(n) of 640 reacts with β- CD to give the 1:4 complex. Poly(tetrahydrofuran) terminated with NH2 groups at both ends also forms the 1:4 complexes both with α-CD and with γ-CD.

    DOI: 10.1246/bcsj.72.1541

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  • Novel Reactions of Divalent Lanthanide Complexes with Arylimines

    KOIZUMI Take-aki, YODA Chikako, HOU Zhaomin, FUKUZAWA Shin-ichi, WAKATSUKI Yasuo

    ( 34 )   284 - 285   1999.5

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  • Highly diastereoselective reduction of chiral (ferrocenylseleno)methyl aryl and alkyl ketones

    M Shirahata, H Yamazaki, S Fukuzawa

    CHEMISTRY LETTERS   ( 3 )   245 - 246   1999.3

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    Chiral (ferrocenylseleno)methyl aryl and alkyl ketones (3) were easily prepared by the reaction of chiral ferrocenylselenenyl triflates and silyl enol ethers. They were reduced by DIBAH to give corresponding beta-hydroxy ferrocenyl selenides (4) in good yields with up to >99% de.

    DOI: 10.1246/cl.1999.245

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  • Synthesis of optical activity 1,2-hetero disubstitued ferrocene compounds and their application to asymmetrics synthesis

    10th IUPAC Symposium on Organometallic Chemistry Directed Toward Organic Synthesis, Versailles, France   1999

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  • Highly diastereoselective reduction of chiral (ferrocenylseleno)methyl aryl and alkyl ketones

    Makoto Shirahata, Hiroshi Yamazaki, Shin-Ichi Fukuzawa

    Chemistry Letters   ( 3 )   245 - 246   1999

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    Chiral (ferrocenylseleno)methyl aryl and alkyl ketones (3) were easily prepared by the reaction of the chiral ferrocenyl-selenenyl triflates and silyl enol ethers. They were reduced by DIBAH to give corresponding β-hydroxy ferrocenyl selenides (4) in good yields with up to &gt
    99% de.

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  • Highly diastereoselective samarium-Reformatsky reaction of chiral alpha-bromoacetyl-2-oxazolidinones with aldehydes

    S Fukuzawa, M Tatsuzawa, K Hirano

    TETRAHEDRON LETTERS   39 ( 38 )   6899 - 6900   1998.9

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    Samarium(II) iodide mediated highly diastereoselective Reformatsky-type reaction of chiral alpha-bromoacetyl-2-oxazolidinones with aldehydes. (C) 1998 Elsevier Science Ltd. all rights reserved.

    DOI: 10.1016/S0040-4039(98)01446-4

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  • Highly diastereoselective samarium-Reformatsky reaction of chiral alpha-bromoacetyl-2-oxazolidinones with aldehydes

    S Fukuzawa, M Tatsuzawa, K Hirano

    TETRAHEDRON LETTERS   39 ( 38 )   6899 - 6900   1998.9

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    Samarium(II) iodide mediated highly diastereoselective Reformatsky-type reaction of chiral alpha-bromoacetyl-2-oxazolidinones with aldehydes. (C) 1998 Elsevier Science Ltd. all rights reserved.

    DOI: 10.1016/S0040-4039(98)01446-4

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  • Chiral 2-(1-dimethylaminoethyl)ferrocenecarbaldehyde as an effective catalyst for asymmetric alkylation of aldehydes with dialkylzinc

    S Fukuzawa, H Kato

    SYNLETT   ( 7 )   727 - 728   1998.7

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    The chiral ferrocenecarbaldehyde bearing an amino group was used as a ligand of diethylzinc in the asymmetric alkylation of aldehydes. It effectively catalyzed the reaction with either aromatic, straight chain or branched aliphatic aldehydes to afford chiral alcohols in good yields with high enantiomeric excess (up to 93 % ee).

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  • Chiral 2-(1-dimethylaminoethyl)ferrocenecarbaldehyde as an effective catalyst for asymmetric alkylation of aldehydes with dialkylzinc

    S Fukuzawa, H Kato

    SYNLETT   ( 7 )   727 - 728   1998.7

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    The chiral ferrocenecarbaldehyde bearing an amino group was used as a ligand of diethylzinc in the asymmetric alkylation of aldehydes. It effectively catalyzed the reaction with either aromatic, straight chain or branched aliphatic aldehydes to afford chiral alcohols in good yields with high enantiomeric excess (up to 93 % ee).

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  • Transesterification of N-acyloxazolidinones with alcohol by lanthanum(III) iodide

    Shin-Ichi Fukuzawa, Yuki Hongo

    Tetrahedron Letters   39 ( 21 )   3521 - 3524   1998.5

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    Transesterification of N-acyloxazolidinones by treatment with an alcohol and lanthanum(III) iodide gives the corresponding esters in good to excellent yields under mild conditions with negligible racemization.

    DOI: 10.1016/S0040-4039(98)00521-8

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  • Transesterification of N-acyloxazolidinones with alcohol by lanthanum(III) iodide

    S Fukuzawa, Y Hongo

    TETRAHEDRON LETTERS   39 ( 21 )   3521 - 3524   1998.5

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    Transesterification of N-acyloxazolidinones by treatment with an alcohol and lanthanum(III) iodide gives the corresponding esters in good to excellent yields under mild conditions with negligible racemization. (C) 1998 Elsevier Science Ltd. All rights reserved.

    DOI: 10.1016/S0040-4039(98)00521-8

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  • Transesterification of N-acyloxazolidinones with alcohol by lanthanum(III) iodide

    S Fukuzawa, Y Hongo

    TETRAHEDRON LETTERS   39 ( 21 )   3521 - 3524   1998.5

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    Transesterification of N-acyloxazolidinones by treatment with an alcohol and lanthanum(III) iodide gives the corresponding esters in good to excellent yields under mild conditions with negligible racemization. (C) 1998 Elsevier Science Ltd. All rights reserved.

    DOI: 10.1016/S0040-4039(98)00521-8

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  • Transesterification of N-Acyl Oxazolidinones with Alcohol by Lanthanum(III) Iidide Reviewed

    Fukuzawa, Hongo

    Tetrahedron Lett.   39 ( 21 )   3521 - 3524   1998.5

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    DOI: 10.1016/S0040-4039(98)00521-8

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  • Asymmetric Methoxyselenenylation of Alkenes with Chiral Ferrocenylselenium Reagents Reviewed

    S. Fukuzawa, K. Takahashi, H. Kato, H. Yamazaki

    J. Org. Chem.   62 ( 22 )   7711 - 7716   1997.11

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    DOI: 10.1021/jo970982z

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  • Scandium(III) triflate-catalyzed Friedel-Crafts alkylation reactions

    T Tsuchimoto, K Tobita, T Hiyama, S Fukuzawa

    JOURNAL OF ORGANIC CHEMISTRY   62 ( 20 )   6997 - 7005   1997.10

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    The Sc(OTf)(3)-catalyzed Friedel-Crafts alkylation reaction with an alcohol, an arenecarbaldehyde or an arenecarbaldehyde acetal as the alkylating agent affords a diarylmethane or an allylbenzene derivative highly selectively. The salient feature of this reaction is that only a catalytic amount of Sc(OTf)(3) can effect the reaction. Furthermore, Sc(OTf)(3) is recoverable and reusable after the synthetic reaction. The Sc(OTf)(3)-catalyzed benzylation using an arenecarbaldehyde and 1,3-propanediol or their acetal affords diarylmethane as a sole product in excellent yields in sharp contrast to the original Friedel-Crafts reaction. Since no reaction occurs in the absence of 1,3-propanediol, the reaction is considered to proceed through a redox process including a hydride shift. The hydride shift mechanism is strongly supported by the experimental evidence. The reaction of benzaldehyde with benzene in the presence of 1,3-propanediol-1,1,3,3,-d(4) gives rise to the deuterium incorporation into the benzylic carbon of diphenylmethane. Worthy of note is that 1,3-propanediol acts as the hydride source. Herein, diphenylmethyl 3-hydroxypropyl ether is assumed to be the most likely intermediate. In this reaction, Sc(OTf)(3) catalyst effectively promotes initial acetal formation, electrophilic aromatic substitution, and successive intramolecular hydride transfer.

    DOI: 10.1021/jo970599u

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  • Preparation of chiral tricarbonyl arene thiol chromium and its application to asymmetric ring opening of meso-epoxides

    S Fukuzawa, H Kato, M Ohtaguchi, Y Hayashi, H Yamazaki

    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1   ( 20 )   3059 - 3063   1997.10

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    Optically active (R,S)- and (S,R)-tricarbonyl (2-[1-(N,N-dimethylamino)ethyl]benzenethiol) chromiums have been prepared in moderate yield by the regioselective lithiation of tricarbonyl [N,N-dimethyl-alpha(R)phenylethylamine]chromium and subsequent reaction of the product with elemental sulfur. The structure of the (R,S)-benzenethiolchromium complex was fully characterized by X-ray crystallography, The chiral benzenethiolchromium complexes reacted with cyclopentene oxide, cyclohexene oxide, 1-methylcyclohexene oxide, cycloheptene oxide and cyclooctene oxide and, after oxidative removal of the chromium moiety, gave the corresponding trans beta-hydroxyalkyl aryl sulfides in high yield with moderate diastereoselectivity, The reaction proceeded without additives and the diastereoselectivity was not affected by the addition of lanthanide(III) complexes which are known to promote the ring-opening of an epoxide with benzenethiol.

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  • Preparation of chiral tricarbonyl arene thiol chromium and its application to asymmetric ring opening of meso-epoxides

    S Fukuzawa, H Kato, M Ohtaguchi, Y Hayashi, H Yamazaki

    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1   ( 20 )   3059 - 3063   1997.10

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    Optically active (R,S)- and (S,R)-tricarbonyl (2-[1-(N,N-dimethylamino)ethyl]benzenethiol) chromiums have been prepared in moderate yield by the regioselective lithiation of tricarbonyl [N,N-dimethyl-alpha(R)phenylethylamine]chromium and subsequent reaction of the product with elemental sulfur. The structure of the (R,S)-benzenethiolchromium complex was fully characterized by X-ray crystallography, The chiral benzenethiolchromium complexes reacted with cyclopentene oxide, cyclohexene oxide, 1-methylcyclohexene oxide, cycloheptene oxide and cyclooctene oxide and, after oxidative removal of the chromium moiety, gave the corresponding trans beta-hydroxyalkyl aryl sulfides in high yield with moderate diastereoselectivity, The reaction proceeded without additives and the diastereoselectivity was not affected by the addition of lanthanide(III) complexes which are known to promote the ring-opening of an epoxide with benzenethiol.

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  • Asymmetric methoxyselenenylation of alkenes with chiral ferrocenylselenium reagents

    S Fukuzawa, K Takahashi, H Kato, H Yamazaki

    JOURNAL OF ORGANIC CHEMISTRY   62 ( 22 )   7711 - 7716   1997.10

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    Asymmetric methoxyselenenylation of alkenes was studied using some chiral ferrocenylselenium compounds which were prepared from chiral ferrocenyl-substituted amine, sulfoxide, oxazoline, and pyrrolidine. The highest diastereoselectivity was observed using the chiral amino-substituted ferrocenylserenium triflates in the reaction with trans-beta-methylstyrene in an excellent yield. The reaction with silyl enol ethers gave chiral alpha-seleno ketone with moderate to excellent selectivities. The beta,gamma-unsaturated ester may be converted into the optically active gamma-alkoxy alpha,beta-unsaturated ester using ammonium persulfate in the presence of a catalytic amount of the chiral diferrocenyl diselenide in low optical yields.

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  • Effective transformation of aldoximes to nitriles by dehydration with 2-methylene-1,3-dioxepane in the presence of a Lewis acid catalyst

    S Fukuzawa, Y Yamaishi, H Furuya, K Terao, F Iwasaki

    TETRAHEDRON LETTERS   38 ( 41 )   7203 - 7206   1997.10

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    The dehydration of aldoximes with 2-methylene-1,3-dioxepane (MDO) proceeds smoothly in the presence of a catalytic amount of Lewis acid such as scandium(III) triflate to give corresponding nitriles in moderate to high yields under mild conditions. (C) 1997 Elsevier Science Ltd.

    DOI: 10.1016/S0040-4039(97)01715-2

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  • Effective transformation of aldoximes to nitriles by dehydration with 2-methylene-1,3-dioxepane in the presence of a Lewis acid catalyst

    S Fukuzawa, Y Yamaishi, H Furuya, K Terao, F Iwasaki

    TETRAHEDRON LETTERS   38 ( 41 )   7203 - 7206   1997.10

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    The dehydration of aldoximes with 2-methylene-1,3-dioxepane (MDO) proceeds smoothly in the presence of a catalytic amount of Lewis acid such as scandium(III) triflate to give corresponding nitriles in moderate to high yields under mild conditions. (C) 1997 Elsevier Science Ltd.

    DOI: 10.1016/S0040-4039(97)01715-2

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  • Scandium(III) Triflate-Catalyzed Friedel-Crafts Alkylation Reactions Reviewed

    T. Tsuchimoto, K. Tobita, T. Hiyama, S. Fukuzawa

    J. Org. Chem.   62 ( 20 )   6997 - 7005   1997.9

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    DOI: 10.1021/jo970599u

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  • Development of Palladium-Catalyzed Reactions for Chalcogen .PI.-Conjugate Polymer.

    小川昭弥, 平尾俊一, 池田拓真, 福沢信一

    日本化学会講演予稿集   72nd ( 2 )   830   1997.3

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  • A facile synthesis of chiral gamma-butyrolactones in extremely high enantioselectivity mediated by samarium(II) iodide

    S Fukuzawa, K Seki, M Tatsuzawa, K Mutoh

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   119 ( 6 )   1482 - 1483   1997.2

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    DOI: 10.1021/ja962965h

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  • A facile synthesis of chiral gamma-butyrolactones in extremely high enantioselectivity mediated by samarium(II) iodide

    S Fukuzawa, K Seki, M Tatsuzawa, K Mutoh

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   119 ( 6 )   1482 - 1483   1997.2

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    DOI: 10.1021/ja962965h

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  • Superacid-catalyzed reductive Friedel-Crafts reaction of arenes using arenecarbaldehyde acetals

    S Fukuzawa, T Tsuchimoto, T Hiyama

    JOURNAL OF ORGANIC CHEMISTRY   62 ( 1 )   151 - 156   1997.1

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    Reaction of 2-aryl-1,3-dioxane with arenes in the presence of a catalytic amount of trifluoromethanesulfonic acid gave the corresponding diarylmethanes in good to excellent yields. The acid-catalyzed Friedel-Crafts benzylation of arenes could altenatively be carried out using arenecarbaldehyde and 1,3-propanediol. The reaction was assumed to proceed through a redox process involving hydride shift from the cyclic acetal moiety to the benzylic carbon. The hydride shift was confirmed by the reaction with 5-ethyl-2-phenyl-4,4,6,6-tetradeuterio-1,3-dioxane, wherein more than 90% deuterium was incorporated into the benzylic carbon of the diphenylmethane. Diphenylmethyl ether Ph(2)CHOCH(2)CH(2)CH(2)OH also reacted with benzene to afford diphenylmethane under the same reaction conditions, suggesting that the ether should be the plausible intermediate that underwent the hydride shift.

    DOI: 10.1021/jo961897e

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  • Superacid-catalyzed reductive Friedel-Crafts reaction of arenes using arenecarbaldehyde acetals

    S Fukuzawa, T Tsuchimoto, T Hiyama

    JOURNAL OF ORGANIC CHEMISTRY   62 ( 1 )   151 - 156   1997.1

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    Reaction of 2-aryl-1,3-dioxane with arenes in the presence of a catalytic amount of trifluoromethanesulfonic acid gave the corresponding diarylmethanes in good to excellent yields. The acid-catalyzed Friedel-Crafts benzylation of arenes could altenatively be carried out using arenecarbaldehyde and 1,3-propanediol. The reaction was assumed to proceed through a redox process involving hydride shift from the cyclic acetal moiety to the benzylic carbon. The hydride shift was confirmed by the reaction with 5-ethyl-2-phenyl-4,4,6,6-tetradeuterio-1,3-dioxane, wherein more than 90% deuterium was incorporated into the benzylic carbon of the diphenylmethane. Diphenylmethyl ether Ph(2)CHOCH(2)CH(2)CH(2)OH also reacted with benzene to afford diphenylmethane under the same reaction conditions, suggesting that the ether should be the plausible intermediate that underwent the hydride shift.

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  • A Facile Synthesis of Chiral g-Butyrolactones in Extremely High Enantioselectivity Mediated by Samarium(II) Diiodide

    IXth International Symposium on Organometallic Chemistry Directed Toward Organic Synthesis   129   1997

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  • Scandium(III) trifluoromethanesulfonate-catalysed reductive Friedel-crafts benzylation of aromatic compounds using arenecarbaldehydes and propane-1,3-diol

    T Tsuchimoto, T Hiyama, S Fukuzawa

    CHEMICAL COMMUNICATIONS   ( 20 )   2345 - 2346   1996.10

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    Scandium(III) trifluoromethanesulfonate catalyses the Friedel-Crafts benzylation of aromatic compounds with arenecarbaldehydes and propane-1,3-diol to produce, through a clean redox process, diarylmethanes in high to excellent yields.

    DOI: 10.1039/cc9960002345

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  • Scandium(III) trifluoromethanesulfonate-catalysed reductive Friedel-crafts benzylation of aromatic compounds using arenecarbaldehydes and propane-1,3-diol

    T Tsuchimoto, T Hiyama, S Fukuzawa

    CHEMICAL COMMUNICATIONS   ( 20 )   2345 - 2346   1996.10

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    Scandium(III) trifluoromethanesulfonate catalyses the Friedel-Crafts benzylation of aromatic compounds with arenecarbaldehydes and propane-1,3-diol to produce, through a clean redox process, diarylmethanes in high to excellent yields.

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  • Samarium(II) triflate as a new reagent for the Grignard-type carbonyl addition reaction

    S Fukuzawa, K Mutoh, T Tsuchimoto, T Hiyama

    JOURNAL OF ORGANIC CHEMISTRY   61 ( 16 )   5400 - 5405   1996.8

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    On treatment of a THF solution of Sm(OTf)(3) with 1 equiv of an organolithium or organomagnesium reagent-at ambient temperature, the purple or deep green solution of the divalent samarium triflate [Sm(OTf)(2)] was readily obtained. For this preparation, s-BuLi was the most effective as was evidenced by the reduction of a-phenylethyl iodide in the presence of HMPA. The Sm(OTf)(2) reagent mediated the Grignard-type reaction effectively in THF/HMPA; alkylation and allylation of ketones or aldehydes with alkyl, allyl, or benzyl halides proceeded via organosamarium intermediates. Diastereoselectivity of the samarium-Grignard reaction was examined using 2-methylcyclohexanone, 4-tert-butylcyclohexanone, and 2-phenylpropanal and was found to be higher in each case than that with SmI2. With 2-methylcyclohexanone, for example, Sm(OTf)(2) gave the greatest ratio of axial alcohol:equatorial alcohol = 99:1, and SmI2 gave a ratio of 91:9. Halides containing an ester or a silyl group were reactive in the Reformatsky- or Peterson-type reaction, respectively, using the Sm(OTf)(2) reagent.

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  • Samarium(II) triflate as a new reagent for the Grignard-type carbonyl addition reaction

    S Fukuzawa, K Mutoh, T Tsuchimoto, T Hiyama

    JOURNAL OF ORGANIC CHEMISTRY   61 ( 16 )   5400 - 5405   1996.8

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    On treatment of a THF solution of Sm(OTf)(3) with 1 equiv of an organolithium or organomagnesium reagent-at ambient temperature, the purple or deep green solution of the divalent samarium triflate [Sm(OTf)(2)] was readily obtained. For this preparation, s-BuLi was the most effective as was evidenced by the reduction of a-phenylethyl iodide in the presence of HMPA. The Sm(OTf)(2) reagent mediated the Grignard-type reaction effectively in THF/HMPA; alkylation and allylation of ketones or aldehydes with alkyl, allyl, or benzyl halides proceeded via organosamarium intermediates. Diastereoselectivity of the samarium-Grignard reaction was examined using 2-methylcyclohexanone, 4-tert-butylcyclohexanone, and 2-phenylpropanal and was found to be higher in each case than that with SmI2. With 2-methylcyclohexanone, for example, Sm(OTf)(2) gave the greatest ratio of axial alcohol:equatorial alcohol = 99:1, and SmI2 gave a ratio of 91:9. Halides containing an ester or a silyl group were reactive in the Reformatsky- or Peterson-type reaction, respectively, using the Sm(OTf)(2) reagent.

    DOI: 10.1021/jo960260s

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  • Samarium(II) triflate as a new reagent for the Grignard-type carbonyl addition reaction

    S Fukuzawa, K Mutoh, T Tsuchimoto, T Hiyama

    JOURNAL OF ORGANIC CHEMISTRY   61 ( 16 )   5400 - 5405   1996.8

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    On treatment of a THF solution of Sm(OTf)(3) with 1 equiv of an organolithium or organomagnesium reagent-at ambient temperature, the purple or deep green solution of the divalent samarium triflate [Sm(OTf)(2)] was readily obtained. For this preparation, s-BuLi was the most effective as was evidenced by the reduction of a-phenylethyl iodide in the presence of HMPA. The Sm(OTf)(2) reagent mediated the Grignard-type reaction effectively in THF/HMPA; alkylation and allylation of ketones or aldehydes with alkyl, allyl, or benzyl halides proceeded via organosamarium intermediates. Diastereoselectivity of the samarium-Grignard reaction was examined using 2-methylcyclohexanone, 4-tert-butylcyclohexanone, and 2-phenylpropanal and was found to be higher in each case than that with SmI2. With 2-methylcyclohexanone, for example, Sm(OTf)(2) gave the greatest ratio of axial alcohol:equatorial alcohol = 99:1, and SmI2 gave a ratio of 91:9. Halides containing an ester or a silyl group were reactive in the Reformatsky- or Peterson-type reaction, respectively, using the Sm(OTf)(2) reagent.

    DOI: 10.1021/jo960260s

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  • Samarium(Ⅱ) Triflate as a New Reagent for Grignard-type Carbonyl Addition Reaction

    Fukuzawa, Mutoh

    第17回有機金属化学国際会議   83   1996.7

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  • Scandium (III) triflate catalyzed Friedel-Crafts alkylation with benzyl and allyl alcohols

    T Tsuchimoto, K Tobita, T Hiyama, SI Fukuzawa

    SYNLETT   ( 6 )   557 - &   1996.6

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    Scandium(III) triflate [Sc(OTf)(3)] was found to be an Friedel-Crafts catalyst for benzylation and allylation reactions of various aromatics with the corresponding alcohols as the alkylating agents.

    DOI: 10.1055/s-1996-5498

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  • Scandium (III) triflate catalyzed Friedel-Crafts alkylation with benzyl and allyl alcohols

    T Tsuchimoto, K Tobita, T Hiyama, SI Fukuzawa

    SYNLETT   ( 6 )   557 - &   1996.6

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    Scandium(III) triflate [Sc(OTf)(3)] was found to be an Friedel-Crafts catalyst for benzylation and allylation reactions of various aromatics with the corresponding alcohols as the alkylating agents.

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  • Synthesis and Activation of Chiral Acetals Using Lanthanide Trifrates

    FURUYA H., FUKUZAWA S., TSUCHIMOTO T., HIYAMA T.

    ( 28 )   312 - 313   1996.5

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  • Highly Enantioselective Ethylation of Aldehydes Cataly2ed by Ferrocenyl Seleno Amino Alcohol

    Fukuzawa, Yamazaki

    中央大学理工学部 研究所論文集   2   55 - 58   1996.4

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  • Highly Enantioselective Ethylation of Aldehydes Cataly2ed by Ferrocenyl Seleno Amino Alcohol

    Fukuzawa, Yamazaki

    中央大学理工学部 研究所論文集   2   55 - 58   1996.4

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  • Alkylation-annulation of halo esters with organometallic reagent/SmI2 couple leading to cycloalkanols: A facile cyclopropanol synthesis from a 3-halo ester

    S Fukuzawa, H Furuya, T Tsuchimoto

    TETRAHEDRON   52 ( 6 )   1953 - 1960   1996.2

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    Transformation of a 3-halo ester to cyclopropanols has been accomplished in excellent yields under mild conditions employing a coupled reagent of samarium(II) diiodide with organometallic reagents. 5- and 6- Halo esters were also transformed into cyclopentanols and cyclohexanols, respectively, in low to moderate yields. The reaction with a 4-halo ester gave 2,2-disubstituted tetrahydrofuran as a major product that resulted from double alkylation followed by cyclization; a substituted cyclobutanol was formed in poor yield.

    DOI: 10.1016/0040-4020(95)01039-4

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  • Alkylation-annulation of halo esters with organometallic reagent/SmI2 couple leading to cycloalkanols: A facile cyclopropanol synthesis from a 3-halo ester

    S Fukuzawa, H Furuya, T Tsuchimoto

    TETRAHEDRON   52 ( 6 )   1953 - 1960   1996.2

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    Transformation of a 3-halo ester to cyclopropanols has been accomplished in excellent yields under mild conditions employing a coupled reagent of samarium(II) diiodide with organometallic reagents. 5- and 6- Halo esters were also transformed into cyclopentanols and cyclohexanols, respectively, in low to moderate yields. The reaction with a 4-halo ester gave 2,2-disubstituted tetrahydrofuran as a major product that resulted from double alkylation followed by cyclization; a substituted cyclobutanol was formed in poor yield.

    DOI: 10.1016/0040-4020(95)01039-4

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  • Novel chiral ligands, diferrocenyl dichalcogenides and their derivatives, for rhodium- and iridium-catalyzed asymmetric hydrosilylation

    Y Nishibayashi, K Segawa, JD Singh, S Fukuzawa, K Ohe, S Uemura

    ORGANOMETALLICS   15 ( 1 )   370 - 379   1996.1

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    As chiral ligands for transition metal complex-catalyzed asymmetric reactions, a variety of novel chiral ferrocenyl chalcogen compounds, which possess planar chirality due to the 1,2-unsymmetrically disubstituted ferrocene structure, have been prepared from chiral ferrocenes. There are seven diferrocenyl dichalcogenides (4-10), nine alkyl or aryl ferrocenyl chalcogenides (11-19), two bis(ferrocenylseleno)alkanes (20 and 21), two 1-(phenylchalcogeno)-1-[2-(diphenylphosphino)ferrocenyl]ethanes (22 and 24), and two 1-(phenylchalcogeno)-1-[1',2-bis(diphenylphosphino)ferrocenyl]ethanes (23 and 25). 2,3-O,O'-Isopropylidene-2,3-dihydroxy-1,4-bis(phenylchalcogeno)butanes (26-28) are also synthesized. The Rh(I) complex-catalyzed hydrosilylation of ketones with diphenylsilane in the presence of these chiral ligands including the reported [R,S;R,S]-bis[2-[1-(dimethylamino)ethyl]ferrocenyl]dichalcogenides (1-3), followed by hydrolysis with dilute HCl, affords the corresponding chiral alcohols (R-configuration) in moderate to quantitative yield with up to 88% enantiomeric excess (ee), Similar treatment of acetophenone in the presence of diferrocenyl dichalcogenides (1, 2, 3, and 10) and a catalytic amount of Ir(I) complex gives chiral 1-phenylethanol of the opposite configuration (S) compared with the Rh case in high yield with up to 23% ee. The new complex prepared from a cationic rhodium compound and the diferrocenyl diselenide (2) shows an activity for asymmetric hydrosilylation of acetophenone to afford 1-phenylethanol in 60% chemical yield with 60% ee. Asymmetric hydrosilylation of imines and asymmetric hydrogenation of an enamide also proceed smoothly using the Rh(I)-diselenide (2) catalytic system to give the corresponding sec-amines and amide with up to 53% and 69% ee, respectively. A catalytic cycle involving the formation of tetracoordinated rhodium(I)-dichalcogenide complex (two Se and two N atoms to one Rh) followed by oxidative addition of the Si-H bond to Rh(I) and carbonyl addition to the produced rhodium(III) hydride complex is proposed for hydrosilylation of ketones.

    DOI: 10.1021/om950533u

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  • Novel Chiral Ligands, Diferrocenyl Diselenides and Their Derivatives,for the Rh- and Ir- Catalyzed Asymmetric Hydrosilylation Reviewed

    Fukuzawa

    Organometallics   15 ( 1 )   370 - 379   1996.1

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    DOI: 10.1021/om950533u

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  • [S,R;S,R]-bis[2-[1-(dimethylamino)ethyl]ferrocenyl]diselenides and their application to asymmetric selenoxide elimination and [2,3]sigmatropic rearrangement (vol 60, pg 4116, 1995)

    Y Nishibayashi, JD Singh, S Fukuzawa, S Uemura

    JOURNAL OF ORGANIC CHEMISTRY   60 ( 25 )   8326 - 8326   1995.12

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  • SYNTHESIS OF CHIRAL DIFERROCENYL DICHALCOGENIDES AND THEIR APPLICATION TO ASYMMETRIC NUCLEOPHILIC RING-OPENING OF MESO-EPOXIDES

    Y NISHIBAYASHI, JD SINGH, S FUKUZAWA, S UEMURA

    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1   ( 22 )   2871 - 2876   1995.11

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    Four novel optically active bis[(R,S)- and (S,R)-2-(1-dimethylaminoethyl)ferrocenyl] dichalcogenides [abbreviated as (R,S)- and (S,R)-(Fc*E), (E = S and Te)], each of which possesses two axial and two central elements of chirality, have been prepared by lithiation of commercially available chiral (1-dimethylaminoethyl)ferrocenes, followed by treatment with elemental sulfur or tellurium and air oxidation, in 42-65% isolated yields, The structure of the di-(S,R)-ferrocenyl disulfide has been fully characterized by X-ray crystallography. Ferrocenyl chalcogenide anions (Fc*E(-)) produced by reduction of the above (Fc*E)(2) and the known (Fc*Se)(2) with LiAlH4 in tetrahydrofuran are found to act as useful stereoselective nucleophiles for ring opening of meso-epoxides such as cyclohexene oxide, cyclopentene oxide, cyclooctene oxide and cis-stilbene oxide to give the corresponding ferrocenyl beta-hydroxyalkyl chalcogenides in high yields with up to 71% diastereoisomeric excess (de). Although the diastereoselectivity depends on the combination of chalcogen atom and meso-epoxide, it is generally higher with E = S and Se than with E = Te. Selenoxide elimination of (S,R)-2-(1-dimethylaminoethyl)ferrocenyl 2-hydroxycyclohexyl selenide (66% de), obtained by the ring opening of cyclohexene oxide with (S,R)-(Fc*Se)(2), gives (S)-cyclohex-2-enol with 60% ee. The S-configuration suggests that the ring opening, by the nucleophilic attack of the chiral ferrocenyl chalcogenide anion on the epoxide carbon, mainly occurs via the least hindered transition state considering the interactions between the epoxide, the 1-dimethylaminoethyl moiety and the ferrocene.

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  • DIRECT SYNTHESIS OF CHIRAL ACETALS FROM CARBONYL-COMPOUNDS AND CHIRAL DIOLS - SEQUENTIAL ONE-POT ASYMMETRIC SILYLCYANATION REACTION CATALYZED BY SCANDIUM(III) TRIFLATE

    S FUKUZAWA, T TSUCHIMOTO, T HOTAKA, T HIYAMA

    SYNLETT   ( 10 )   1077 - &   1995.10

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    Chiral acetal formation followed by cyanation of carbonyl compounds was successfully carried out in one-pot using chiral diols, scandium(III) triflate and then trimethylsilyl cyanide.

    DOI: 10.1055/s-1995-5184

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  • Synthesis of Chiral Diferrocenyl Dichalcogenides and Their Application to Asymmetric Nucleophilic Ring Opening of meso-Epoxide Reviewed

    Fukuzawa

    J. Chem. Soc. Perkin Trans I   ( 22 )   2871   1995.10

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  • DIRECT SYNTHESIS OF CHIRAL ACETALS FROM CARBONYL-COMPOUNDS AND CHIRAL DIOLS - SEQUENTIAL ONE-POT ASYMMETRIC SILYLCYANATION REACTION CATALYZED BY SCANDIUM(III) TRIFLATE

    S FUKUZAWA, T TSUCHIMOTO, T HOTAKA, T HIYAMA

    SYNLETT   ( 10 )   1077 - &   1995.10

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    Chiral acetal formation followed by cyanation of carbonyl compounds was successfully carried out in one-pot using chiral diols, scandium(III) triflate and then trimethylsilyl cyanide.

    DOI: 10.1055/s-1995-5184

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  • A Facile Conversion of Substituted Cyclobutanones to Cyclopentanones by CH2I2/SmI2 System,

    Fukuzawa, Tsuchimoto

    Tetrahedron Lett.   36 ( 33 )   5937 - 5938   1995.9

  • A Facile One-pot Synthesis of Chiral Acetals and Subsequent C-C Bond Forming Reaction Catalyzed by Ln(OTf)

    Fukuzawa, Tsuchimoto

    第8回有機合成指向有機金属化学国際会議   96   1995.8

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  • A FACILE CONVERSION OF SUBSTITUTED CYCLOBUTANONES TO CYCLOPENTANONES BY CH2I2/SMI2 SYSTEM

    S FUKUZAWA, T TSUCHIMOTO

    TETRAHEDRON LETTERS   36 ( 33 )   5937 - 5938   1995.8

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    Ring expansion reaction of a substituted cyclobutanone with CH2I2 and SmI2 proceeded cleanly in extended reaction time (15 h) to afford the corresponding cyclopentanone in good yield, whereas short reaction time (0.5 h) produced a mixture of iodohydrin and cyclopentanone.

    DOI: 10.1016/0040-4039(95)01199-R

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  • Synthesis of [R,S;R,S]- and [S,R;S,R]-Bis[2-[1-(dimethylamino)ethyl]ferrocenyl] Diselenides and Their Application to Asymmetric Selenoxide Elimination and [2,3]Sigmatropic Rearrangement

    Yoshiaki Nishibayashi, Jai Deo Singh, Shin-ichi Fukuzawa, Sakae Uemura

    Journal of Organic Chemistry   60 ( 13 )   4114 - 4120   1995.6

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    Novel optically-active bis[2-[1-(dimethylamino)ethyl]ferrocenyl] diselenides ([R,S
    R,S] and [S,R
    S,R]), each of which possesses two axial and two central elements of chirality, have been prepared by lithiation of commercially available chiral [1-(dimethylamino)ethyl]ferrocenes, followed by reaction with elemental selenium and air oxidation, in 77–80% isolated yields. The structure of the [S,R
    S,R]-bisferrocenyl diselenide has been fully characterized by X-ray crystallography. Six chiral ferrocenyl vinylic selenides and six chiral allylic ferrocenyl selenides have been newly prepared by reaction of the diselenides with the corresponding propiolate derivatives and allylic halides. The oxidation of the vinylic selenides with m-chloroperbenzoic acid in various organic solvents produces axially chiral allenecarboxylic esters via asymmetric selenoxide elimination in 27–59% chemical yields with high enantioselectivities (up to 89% ee). Similar treatment of the allylic selenides afforded the corresponding chiral allylic alcohols via asymmetric [2,3]sigmatropic rearrangement in 28–82% chemical yields with high enantioselectivities (up to 89% ee). The observed high enantioselectivities indicate that oxidation proceeds highly diastereoselectively, that the resultant chiral selenoxides are slow to racemize, and also that selenoxide elimination and [2,3]sigmatropic rearrangement proceed with little loss of optical activity. © 1995, American Chemical Society. All rights reserved.

    DOI: 10.1021/jo00118a031

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  • SYNTHESIS OF [R,S-R,S]-BIS[2-[1-(DIMETHYLAMINO)ETHYL]FERROCENYL]DISELENIDES AND [S,R-S,R]-BIS[2-[1-(DIMETHYLAMINO)ETHYL]FERROCENYL]DISELENIDES AND THEIR APPLICATION TO ASYMMETRIC SELENOXIDE ELIMINATION AND [2,3]SIGMATROPIC REARRANGEMENT

    Y NISHIBAYASHI, JD SINGH, S FUKUZAWA, S UEMURA

    JOURNAL OF ORGANIC CHEMISTRY   60 ( 13 )   4114 - 4120   1995.6

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    Novel optically-active bis[2-[1-(dimethylamino)ethyl]ferrocenyl] diselenides ([R,S;R,S] and [S,R;S,R]), each of which possesses two axial and two central elements of chirality, have been prepared by lithiation of commercially available chiral [1-(dimethylamino)ethyl]ferrocenes, followed by reaction with elemental selenium and air oxidation, in 77-80% isolated yields. The structure of the [S,R;S,R]-bisferrocenyl diselenide has been fully characterized by X-ray crystallography. Six chiral ferrocenyl vinylic selenides and six chiral allylic ferrocenyl selenides have been newly prepared by reaction of the diselenides with the corresponding propiolate derivatives and allylic halides. The oxidation of the vinylic selenides with m-chloroperbenzoic acid in various organic solvents produces axially chiral allenecarboxylic esters via asymmetric selenoxide elimination in 27-59% chemical yields with high enantioselectivities (up to 89% ee). Similar treatment of the allylic selenides afforded the corresponding chiral allylic alcohols via asymmetric [2,3]sigmatropic rearrangement in 28-82% chemical yields with high enantioselectivities (up to 89% ee). The observed high enantioselectivities indicate that oxidation proceeds highly diastereoselectively, that the resultant chiral selenoxides are slow to racemize, and also that selenoxide elimination and [2,3]sigmatropic rearrangement proceed with little loss of optical activity.

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  • Reactivities and Stereoselectivities of Organolanthanide Speecies Generated in situ from Organic Halides and Divalent Lanthanide Trifrates

    ITOU N., MUTOU K., FUKUZAWA S.

    ( 26 )   326 - 327   1995.5

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  • FERROCENYLSELENO AMINO-ALCOHOLS AS NEW CATALYSTS FOR THE HIGHLY ENANTIOSELECTIVE ALKYLATION OF ALDEHYDES

    S FUKUZAWA, K TSUDZUKI

    TETRAHEDRON-ASYMMETRY   6 ( 5 )   1039 - 1042   1995.5

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    Language:English   Publishing type:Article, review, commentary, editorial, etc. (scientific journal)   Publisher:PERGAMON-ELSEVIER SCIENCE LTD  

    A chiral or a diastereomeric mixture of 1-[1-(N'N-dimethylaminoethyl)-2-(2'-hydroxyalkylseleno)]-ferrocene (DASF) was easily prepared by the chiral diferrocenyldiselenide (1)and:epoxides. DASF derivatives efficiently catalyzed the ethylation of aldehydes with diethyl zinc to give the secondary alcohols in good to excellent yield with up to 99 % ee.

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  • A Facile One-pot Synthesis of Chiral Acetals and Subsequent C-C Bond Forming Reaction Catalyzed by Ln(OTf)

    第8回有機合成指向有機金属化学国際会議   96   1995

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  • Ferrocenylseleno amino alcohols as new catalysts for the highly enantioselective alkylation of aldehydes

    Shin-ichi Fukuzawa, Kiyoshi Tsudzuki

    Tetrahedron: Asymmetry   6 ( 5 )   1039 - 1042   1995

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    A chiral or a diastereomeric mixture of 1-[1-N,N-dimethylaminoethyl)-2-(2′-hydroxyalkylseleno)]-ferrocene (DASF) was easily prepared by the chiral diferrocenyldiselenide (1) and epoxides. DASF derivatives efficiently catalyzed the ethylation of aldehydes with diethyl zinc to give the secondary alcohols in good to excellent yield with up to 99 % ee. © 1995.

    DOI: 10.1016/0957-4166(95)00119-A

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  • Highly selective asymmetric intramolecular selenocyclisation

    Yoshiaki Nishibayashi, Sanjay Kumar Srivastava, Hiroya Takada, Shin-Ichi Fukuzawa, Sakae Uemura

    Journal of the Chemical Society, Chemical Communications   ( 22 )   2321 - 2322   1995

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    Asymmetric intramolecular selenocyclisation of alkenoic acids, alkenols and olefinic urethanes using chiral ferrocenylselenenyl cations proceeds smoothly to give the corresponding lactones, cyclic ethers and nitrogen-heterocyclic compounds, respectively, in moderate yields with very high diastereoselectivities.

    DOI: 10.1039/C39950002321

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  • Highly selective asymmetric intramolecular selenocyclisation

    Yoshiaki Nishibayashi, Sanjay Kumar Srivastava, Hiroya Takada, Shin-Ichi Fukuzawa, Sakae Uemura

    Journal of the Chemical Society, Chemical Communications   ( 22 )   2321 - 2322   1995

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    Asymmetric intramolecular selenocyclisation of alkenoic acids, alkenols and olefinic urethanes using chiral ferrocenylselenenyl cations proceeds smoothly to give the corresponding lactones, cyclic ethers and nitrogen-heterocyclic compounds, respectively, in moderate yields with very high diastereoselectivities.

    DOI: 10.1039/C39950002321

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  • A HIGHLY SELECTIVE ASYMMETRIC METHOXYSELENYLATION OF ALKENES WITH A CHIRAL FERROCENYLSELENIUM REAGENT

    S FUKUZAWA, Y KASUGAHARA, S UEMURA

    TETRAHEDRON LETTERS   35 ( 50 )   9403 - 9406   1994.12

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    Chiral diferrocenyl diselenide was easily converted into chiral ferrocenylselenyl bromide by treatment of bromine in CH2Cl2/CCl4 at -78 degrees C. This chiral electrophilic selenium reagent reacted with alkenes in the presence of methanol with high facial selectivity to afford selenomethoxylated adducts in moderate yields.

    DOI: 10.1016/S0040-4039(00)78554-6

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  • A HIGHLY SELECTIVE ASYMMETRIC METHOXYSELENYLATION OF ALKENES WITH A CHIRAL FERROCENYLSELENIUM REAGENT

    S FUKUZAWA, Y KASUGAHARA, S UEMURA

    TETRAHEDRON LETTERS   35 ( 50 )   9403 - 9406   1994.12

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    Chiral diferrocenyl diselenide was easily converted into chiral ferrocenylselenyl bromide by treatment of bromine in CH2Cl2/CCl4 at -78 degrees C. This chiral electrophilic selenium reagent reacted with alkenes in the presence of methanol with high facial selectivity to afford selenomethoxylated adducts in moderate yields.

    DOI: 10.1016/S0040-4039(00)78554-6

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  • Grignard-type Reaction mediated by Samarium(II) Triflate. In situ Preparation and Reaction of Organosamarium Reagents Reviewed

    Fukuzawa, Tsuchimoto, Kanai

    Chem. Lett.   ( 11 )   1981 - 1984   1994.11

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    DOI: 10.1246/cl.1994.1981

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  • PREPARATION OF SAMARIUM(II) TRIFLATE AND IT MEDIATED GRIGNARD-TYPE REACTION - IN-SITU FORMATION AND REACTION OF NEW ORGANOSAMARIUM REAGENTS

    SI FUKUZAWA, T TSUCHIMOTO, T KANAI

    CHEMISTRY LETTERS   ( 11 )   1981 - 1984   1994.11

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    Samarium(II) triflate was readily prepared by the reaction of samarium(III) triflate with sec-butyllithium at room temperature in THF. Its reducing ability was examined by pinacol coupling of carbonyl compounds. Sm(OTf)(2) mediated Grignard-type reaction in THF-HMPA effectively; alkylation and allylation of ketones or aldehydes by simple alkyl, allyl, and benzyl halides proceeded via organosamarium intermediates.

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  • Pd触媒によるC-Nヘテロクロスカップリング反応

    福沢信一

    Organometallic News   ( 3 )   125   1994.11

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  • ヨウ化サマリウム(Ⅱ)を用いるBarbier型の反応の反応機構機サマリウム中間体機構に対する証拠―

    福沢信一

    化学と工業   47 ( 9 )   1447 - 1448   1994.9

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  • YTTERBIUM TRIFLUOROMETHANESULFONATE MEDIATED CROSS-ALDOL REACTION BETWEEN KETONES AND ALDEHYDES

    S FUKUZAWA, T TSUCHIMOTO, T KANAI

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   67 ( 8 )   2227 - 2232   1994.8

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    The cross-aldol reaction between a ketone and an aldehyde proceeded smoothly with threo diastereoselection favorably mediated by ytterbium trifluoromethanesulfonate and tertiary amine in diethyl ether or in dichloromethane. A ytterbium enolate was trapped with chlorotrimethylsilane to afford a silyl enol ether.

    DOI: 10.1246/bcsj.67.2227

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  • YTTERBIUM TRIFLUOROMETHANESULFONATE MEDIATED CROSS-ALDOL REACTION BETWEEN KETONES AND ALDEHYDES

    S FUKUZAWA, T TSUCHIMOTO, T KANAI

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   67 ( 8 )   2227 - 2232   1994.8

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    The cross-aldol reaction between a ketone and an aldehyde proceeded smoothly with threo diastereoselection favorably mediated by ytterbium trifluoromethanesulfonate and tertiary amine in diethyl ether or in dichloromethane. A ytterbium enolate was trapped with chlorotrimethylsilane to afford a silyl enol ether.

    DOI: 10.1246/bcsj.67.2227

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  • Pd触媒によるC-Nヘテロクロスカップリング反応

    福沢信一

    Organometallic News   ( 3 )   125   1994.6

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  • RHODIUM(I)-CATALYZED ASYMMETRIC HYDROSILYLATION OF KETONES USING NEW DIFERROCENYL DICHALCOGENIDES (R,S)-([EC(5)H(3)CHME(NME(2))]FE(C5H5))(2) (E=S, SE, TE), AS CHIRAL LIGANDS

    Y NISHIBAYASHI, JD SINGH, K SEGAWA, S FUKUZAWA, S UEMURA

    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS   ( 11 )   1375 - 1376   1994.6

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    The new chiral compounds, (R,S)-di[2-(1-dimethylaminoethyl)ferrocenyl] dichalcogenides (R,S)-{[EC(5)H(3)CHMe(NMe(2))]Fe(C5H5)}, (E = S, Se, Te), work effectively as chiral ligands for the rhodium(i)-catalysed asymmetric hydrosilylation of alkyl aryl ketones resulting in high enantiomeric excess and moderate chemical yields.

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  • Synthesis of chiral diferrocenyl diselenides and their application to asymmetric reactions

    Yoshiaki Nishibayashi, Jai Deo Singh, Sakae Uemura, Shin-ichi Fukuzawa

    Tetrahedron Letters   35 ( 19 )   3115 - 3118   1994.5

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    Two optically active diferrocenyl diselenides, each of which possesses two chiral centers, were newly prepared from commercial 1-(dimethylamino)ethylferrocenes and applied to induce highly enantioselective selenoxide elimination producing axially chiral allenecarboxylic esters. © 1994.

    DOI: 10.1016/S0040-4039(00)76844-4

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  • SYNTHESIS OF CHIRAL DIFERROCENYL DISELENIDES AND THEIR APPLICATION TO ASYMMETRIC REACTIONS

    Y NISHIBAYASHI, JD SINGH, S UEMURA, S FUKUZAWA

    TETRAHEDRON LETTERS   35 ( 19 )   3115 - 3118   1994.5

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    Two optically active diferrocenyl diselenides, each of which possesses two chiral centers, were newly prepared from commercial 1-(dimethylamino)ethylferrocenes and applied to induce highly enantioselective selenoxide elimination producing axially chiral allenecarboxylic esters.

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  • Rhodium(I)-catalysed asymmetric hydrosilylation of ketones using new diferrocenyl dichalcogenides (R,S)-{[EC5H3CHMe(NMe 2)]Fe(C5H5)}2 (E=S, Se, Te), as chiral ligands

    Yoshiaki Nishibayashi, Jai Deo Singh, Kyohei Segawa, Shin-Ichi Fukuzawa, Sakae Uemura

    Journal of the Chemical Society, Chemical Communications   ( 11 )   1375 - 1376   1994

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    The new chiral compounds, (R,S)-di[2-(1-dimethylaminoethyl)ferrocenyl] dichalcogenides (R,S)-{[EC5H3CHMe(NMe2)] Fe(C5H5)}2 (E=S, Se, Te), work effectively as chiral ligands for the rhodium(I)-catalysed asymmetric hydrosilylation of alkyl aryl ketones resulting in high enantiomeric excess and moderate chemical yields.

    DOI: 10.1039/C39940001375

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  • SAMARIUM(II) DIIODIDE INDUCED INTRAMOLECULAR COUPLING REACTION OF HALOCETALS LEADING TO THE SYNTHESIS OF GAMMA-LACTONES

    S FUKUZAWA, T TSUCHIMOTO

    SYNLETT   56 ( 10 )   803 - 804   1993.10

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    Treatment of a mixture of a haloacetal (1) and tert-butanol with 2.5 equiv of samarium (II) diiodide in THF-HMPA gave in good conversion the cyclic acetal (2), which was transformed to the gamma-lactone (3) with Jones oxidation (overall yield, 70-90 %). The stereochemistry of the 2,4- (2;R1=H, R2=Me, Et) or 2,3-disubustituted lactones were predominantly trans (trans: cis=86:14-98:2).

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  • Samarium(II) Diiodide Induced Intramolecular Couplins Roc Chum of Haloacetals Reviewed

    Fukuzawa, Tsuchimoto

    Synlett   ( 10 )   803 - 804   1993.10

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  • Samarium(Ⅱ) Diiodide Induced Intramolecular Couplins Roc Chum of Haloacetals

    Fukuzawa, Tsuchimoto

    Synlett   ( 10 )   803 - 804   1993.10

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  • Samarium(Ⅱ) Diiodide Induced Intramolecular Coupling of Haloacetals Leading to Synthesis of γ-Lactones

    Fukuzawa, Tsuchimoto

    第7回有機合成指向有機金属化学国際会議   56   1993.9

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  • Lithium Benzenetellurolate-induced Reformatsky-type reaction in the presence of cerium trichloride

    Fukuzawa, Hirai

    J. Chem Soc. Pevkin 1   ( 17 )   1963 - 1965   1993.8

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  • Lithium Benzenetellurolate-induced Reformatsky-type reaction in the presence of cerium trichloride Reviewed

    Fukuzawa, Hirai

    J. Chem Soc. Pevkin 1   ( 17 )   1963 - 1965   1993.8

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  • SAMARIUM DIIODIDE PROMOTED ALPHA-METHYLENE-GAMMA-LACTONE SYNTHESIS

    S FUKUZAWA, S SAKAI

    NIPPON KAGAKU KAISHI   ( 5 )   513 - 515   1993

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    Samarium diiodide promoted reductive coupling between ethyl 2-(bromomethyl)acrylate (1) and carbonyl compounds (2) was studied. The 2-ethoxycarbonyl allylation with benzaldehyde, hexanal, acetophenane, and benzophenone proceeded in tetrahydrofuran-hexamethyl-phosphoric triamide at -78-degrees-C to room temperature, and the corresponding alpha-methylene-gamma-butyrolactones (3) were produced in moderate yields. However, the reaction with cyclohexanone and diethyl ketone only resulted in a reductive dimerization of 1 ; no desired 3 were obtained and diethyl 2, 5-bis(methylene)hexanedioate was produced in 50-70% yields. When the reaction was carried out by using ethyl 2-(acetoxymethyl)acrylate 7 instead of 1 as a precursor in the presence of catalytic amount of tetrakis(triphenylphosphine)palladium complex, the corresponding 3 were obtained from the reaction not only with benzaldehyde, hexanal, and acetophenone but also cyclohexanone which did not give 3 in the reaction with 1.

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  • HIGHLY REGIOSELECTIVE ALLYLATION OF ALPHA-ENONES AND EPOXIDES WITH LITHIUM TETRAALLYLLANTHANOID ATE COMPLEX

    S FUKUZAWA, S SAKAI

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   65 ( 12 )   3308 - 3314   1992.12

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    Tetraallyllanthanoid ate complex (1), which was readily prepared in situ from tetraallyltin, lanthanoid trichloride, and butyllithium in tetrahydrofuran (THF), reacts smoothly with alpha-enones (3-11) with a high degree of 1,2-regioselectivity (1,2: 1,4=>99: 1) to give 1,5-diene-3-ols in good to excellent yields. The mechanistic study with 4,4-(ethylenedioxy)-2,6-dimethyl-2,5-cyclohexadienone (29) as a probe suggests that single electron transfer (SET) may be involved in this carbonyl allylation reaction with 1. Allylative ring opening of styrene oxide with 1 occurs at the more subsituted carbon (alpha-attack) in higher selectivity (alpha: beta=85: 15) than with allyllithium and allylmagnesium bromide in diethyl ether. The complex 1 reacts with 3,4-epoxy-1-butene (35) in diethyl ether predominantly at the most substituted carbon of the oxirane to give 3-hydroxymethyl-1,5-hexadiene (36) together with 1,6-heptadien-3-ol (37), (E) and (Z)-2,6-heptadienols (38) (36: 37:38=87: 9:4)

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  • HIGHLY REGIOSELECTIVE ALLYLATION OF ALPHA-ENONES AND EPOXIDES WITH LITHIUM TETRAALLYLLANTHANOID ATE COMPLEX

    S FUKUZAWA, S SAKAI

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   65 ( 12 )   3308 - 3314   1992.12

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    Tetraallyllanthanoid ate complex (1), which was readily prepared in situ from tetraallyltin, lanthanoid trichloride, and butyllithium in tetrahydrofuran (THF), reacts smoothly with alpha-enones (3-11) with a high degree of 1,2-regioselectivity (1,2: 1,4=>99: 1) to give 1,5-diene-3-ols in good to excellent yields. The mechanistic study with 4,4-(ethylenedioxy)-2,6-dimethyl-2,5-cyclohexadienone (29) as a probe suggests that single electron transfer (SET) may be involved in this carbonyl allylation reaction with 1. Allylative ring opening of styrene oxide with 1 occurs at the more subsituted carbon (alpha-attack) in higher selectivity (alpha: beta=85: 15) than with allyllithium and allylmagnesium bromide in diethyl ether. The complex 1 reacts with 3,4-epoxy-1-butene (35) in diethyl ether predominantly at the most substituted carbon of the oxirane to give 3-hydroxymethyl-1,5-hexadiene (36) together with 1,6-heptadien-3-ol (37), (E) and (Z)-2,6-heptadienols (38) (36: 37:38=87: 9:4)

    DOI: 10.1246/bcsj.65.3308

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  • A FACILE CYCLOPROPANOL SYNTHESIS FROM BETA-HALO ESTER WITH GRIGNARD REAGENT-SAMARIUM(II) DIIODIDE COUPLE

    S FUKUZAWA, Y NIIMOTO, S SAKAI

    TETRAHEDRON LETTERS   32 ( 52 )   7691 - 7694   1991.12

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    Transformation of alpha,beta-halo ester to the cyclopropanols by a coupled reagent of samarium(II) diiodide with Grignard reagent in tetrahydrofuran-hexamethylphosphoric triamide was very successfully under mild conditions.

    DOI: 10.1016/0040-4039(91)80567-P

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  • A FACILE CYCLOPROPANOL SYNTHESIS FROM BETA-HALO ESTER WITH GRIGNARD REAGENT-SAMARIUM(II) DIIODIDE COUPLE

    S FUKUZAWA, Y NIIMOTO, S SAKAI

    TETRAHEDRON LETTERS   32 ( 52 )   7691 - 7694   1991.12

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    Transformation of alpha,beta-halo ester to the cyclopropanols by a coupled reagent of samarium(II) diiodide with Grignard reagent in tetrahydrofuran-hexamethylphosphoric triamide was very successfully under mild conditions.

    DOI: 10.1016/0040-4039(91)80567-P

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  • A Faule Cyclo propanol Synthesis From β-Halo Ester with Grignard Reagent SmI2 couple

    S.Fukuzawa, Y.Niimoto, S.Sakai

    6th IUPAC Sympo on organomet. Chem directd Toward org syn.   B86 Abstract   1991.8

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  • A Faule Cyclo propanol Synthesis From β-Halo Ester with Grignard Reagent SmI2 couple Reviewed

    S.Fukuzawa, Y.Niimoto, S.Sakai

    6th IUPAC Sympo on organomet. Chem directd Toward org syn.   B86 Abstract   1991.8

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  • A Fa●k cyclopropanol syuhesis fromβ- Halo Ester with Grignerd Reesent-Sam●rium diiodide Couple

    第38回有機金属討論会   B115   286 - 289   1991

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  • ACETOXYTELLURINATION OF ALKENES WITH TELLURIUM TETRACHLORIDE AND LITHIUM-ACETATE

    S FUKUZAWA, KJ IRGOLIC, DH OBRIEN

    ORGANOMETALLICS   9 ( 12 )   3073 - 3080   1990.12

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    DOI: 10.1021/om00162a019

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  • ACETOXYTELLURINATION OF ALKENES WITH TELLURIUM TETRACHLORIDE AND LITHIUM-ACETATE

    S FUKUZAWA, KJ IRGOLIC, DH OBRIEN

    ORGANOMETALLICS   9 ( 12 )   3073 - 3080   1990.12

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    DOI: 10.1021/om00162a019

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  • PI-ALLYL LANTHANOID ATE COMPLEX AS A NEW HIGHLY 1,2-REGIOSELECTIVE ALLYL TRANSFER AGENT FOR ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS

    S FUKUZAWA, K SATO, T FUJINAMI, S SAKAI

    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS   ( 13 )   939 - 940   1990.7

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    DOI: 10.1039/c39900000939

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  • Surface-active Organo Manganese and Cobalt Complexes (1+) Having a Long Chain Alkyl Group Reviewed

    S.Sakai

    Chem. Lett.   1970   173 - 176   1990.7

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    DOI: 10.1246/cl.1990.173

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  • PI-ALLYL LANTHANOID ATE COMPLEX AS A NEW HIGHLY 1,2-REGIOSELECTIVE ALLYL TRANSFER AGENT FOR ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS

    S FUKUZAWA, K SATO, T FUJINAMI, S SAKAI

    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS   ( 13 )   939 - 940   1990.7

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    DOI: 10.1039/c39900000939

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  • Anion-Conducting Film Composed Poly (Vinyl chloride), Quarternary Ammonium Iodide, and Organotin Compound Reviewed

    T.Fujinami

    Chem. Lett.   1990 ( 1 )   127 - 128   1990.6

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    Anionic conductivity of poly(vinyl chloride)-tetrabutylammonium iodide composite film has been remarkably increased by the addition of organotin compounds. At a high content of tributyltin iodide, the conductivity has been enhanced up to the order of 10−4 S/cm at 25 °C.

    DOI: 10.1246/cl.1990.127

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  • A Facile Preparation of Allylic Phenyl Selenides from Allylic Acetates and Diphenyl Diselenide Promoted by Samarium(II) Diiodide in the presence of Palladium Catalyst Reviewed

    S.Fukuzawa, T.Fujinami, S.Sakai

    Chem. Lett.   927 - 938   1990.4

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    DOI: 10.1246/cl.1990.927

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  • Preparation and Properties of Surface Active Organo cobalt complexes having Long-chain Alkyl Group Reviewed

    S.Sakai

    Appl. Organomet chem.   1990   35 - 40   1990.4

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  • A Facile Preparation of Allylic Phenyl Selenides from Allylic Acetates and Diphenyl Diselenide Promoted by Samarium(II) Diiodide in the presence of Palladium Catalyst Reviewed

    S.Fukuzawa, T.Fujinami, S.Sakai

    Chem. Lett.   927 - 938   1990.4

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  • DIRECT PREPARATION OF LANTHANOID ESTER HOMOENOLATES FROM 3-HALO ESTERS AND LANTHANOID METALS - THEIR HOMO-REFORMATSKY-TYPE REACTION WITH CARBONYL-COMPOUNDS

    S FUKUZAWA, N SUMIMOTO, T FUJINAMI, S SAKAI

    JOURNAL OF ORGANIC CHEMISTRY   55 ( 5 )   1628 - 1631   1990.3

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    DOI: 10.1021/jo00292a043

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  • DIRECT PREPARATION OF LANTHANOID ESTER HOMOENOLATES FROM 3-HALO ESTERS AND LANTHANOID METALS - THEIR HOMO-REFORMATSKY-TYPE REACTION WITH CARBONYL-COMPOUNDS

    S FUKUZAWA, N SUMIMOTO, T FUJINAMI, S SAKAI

    JOURNAL OF ORGANIC CHEMISTRY   55 ( 5 )   1628 - 1631   1990.3

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    DOI: 10.1021/jo00292a043

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  • SURFACE-ACTIVE ORGANO MANGANESE AND COBALT COMPLEXES(1+) HAVING A LONG-CHAIN ALKYL GROUP

    S SAKAI, H KOZAWA, H SAEKI, S FUKUZAWA, T FUJINAMI

    CHEMISTRY LETTERS   ( 2 )   173 - 176   1990.2

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    DOI: 10.1246/cl.1990.173

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  • Samarium Diiodide Indnted reductime Cleavage of Se-Se and Te-Te hond of pipleml Diselch●de and Diklluride

    Heteroatom.chem   1990 ( 1 )   491 - 495   1990

  • Samarium (II) diiodide‐induced reductive cleavage of SeSe and TeTe bond in diphenyl diselenide and ditelluride leading to a samarium phenylselenolate and tellurolate: Preparation of unsymmetrical alkylphenyl selenides and tellurides

    Shin‐Ichi Fukuzawa, Yasuhiko Niimoto, Tatsuo Fujinami, Shizuyoshi Sakai

    Heteroatom Chemistry   1 ( 6 )   491 - 495   1990

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    Diphenyl diselenide and diphenyl ditelluride were reduced by samarium (II) diiodide in tetrahydrofuran‐hexamethylphosphoric triamide to produce samarium phenylselenolate and samarium phenyltellurolate, respectively. This new selenolate or tellurolate anion species reacted smoothly with alkyl, allyl, and benzyl halides to give alkyl‐, allyl‐, and benzylphenyl selenides or tellurides in good yields under mild and neutral conditions. The samarium selenolate reacted with α‐halo ketones to give the corresponding α‐phenylseleno ketones. 1,4‐Addition with α,β‐enones proceeded to give 3‐phenylseleno ketones in moderate yields. Isolation of phenylselenotributyltin or phenylseleno‐trimethylsilane by transmetalation with tributyltin iodide or trimethylchlorosilane, respectively, suggested the presence of the samarium selenolate species. Copyright © 1990 VCH Publishers, Inc.

    DOI: 10.1002/hc.520010611

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  • PREPARATION AND PROPERTIES OF SURFACE-ACTIVE ORGANOCOBALT COMPLEXES HAVING LONG-CHAIN ALKYL-GROUPS

    S SAKAI, H TAKAYANAGI, N SUMIMOTO, S FUKUZAWA, T FUJINAMI, H SAEKI

    APPLIED ORGANOMETALLIC CHEMISTRY   4 ( 1 )   35 - 42   1990

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    DOI: 10.1002/aoc.590040107

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  • 1.2-Regioselechve Allylation of α.β- Emones with Allyl-lanthanoid Corpletes

    第37回有機金属討論会   PB103   256 - 258   1990

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  • Aniu●-Conducting Film Comp● Poly (Vinyl Chluvide), Qualernay Ammunium Iodrde, and Orgamu G● Compo●

    Chem. Lett.   1990   127 - 128   1990

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  • LANTHANOID(III) TRICHLORIDE-TIN(II) CHLORIDE MEDIATED CYCLO-ADDITION REACTION OF ALPHA, ALPHA'-DIBROMO KETONES WITH 1,3-DIENES OR ENAMINES

    S FUKUZAWA, M FUKUSHIMA, T FUJINAMI, S SAKAI

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   62 ( 7 )   2348 - 2352   1989.7

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    DOI: 10.1246/bcsj.62.2348

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  • LANTHANOID(III) TRICHLORIDE-TIN(II) CHLORIDE MEDIATED CYCLO-ADDITION REACTION OF ALPHA, ALPHA'-DIBROMO KETONES WITH 1,3-DIENES OR ENAMINES

    S FUKUZAWA, M FUKUSHIMA, T FUJINAMI, S SAKAI

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   62 ( 7 )   2348 - 2352   1989.7

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    DOI: 10.1246/bcsj.62.2348

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  • Studies on Surface-Active Organotransition Metallics

    S.Sakai

    The 19th World Congress of The Intermational Society for Fat Research   6S22   726 - 732   1988.9

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  • Studies on Surface-Active Organotransition Metallics Reviewed

    S.Sakai

    The 19th World Congress of The Intermational Society for Fat Research   6S22   726 - 732   1988.9

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  • SAMARIUM(II) DI-IODIDE INDUCED REDUCTIVE COUPLING OF ALPHA,BETA-UNSATURATED ESTERS WITH CARBONYL-COMPOUNDS LEADING TO A FACILE SYNTHESIS OF GAMMA-LACTONE

    S FUKUZAWA, A NAKANISHI, T FUJINAMI, S SAKAI

    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1   ( 7 )   1669 - 1675   1988.7

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    DOI: 10.1039/p19880001669

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  • A NEW TYPE OF SURFACE-ACTIVE ORGANOTRANSITION METAL-COMPLEX - (LONG-CHAIN ALKYL SUBSTITUTED BENZENE) (CYCLOPENTADIENYL) IRON(1+) CATIONIC COMPLEXES

    S SAKAI, H KOZAWA, Y YOSHINAGA, K KOSUGI, S FUKUZAWA, T FUJINAMI

    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS   ( 10 )   663 - 664   1988.5

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  • A NEW TYPE OF SURFACE-ACTIVE ORGANOTRANSITION METAL-COMPLEX - (LONG-CHAIN ALKYL SUBSTITUTED BENZENE) (CYCLOPENTADIENYL) IRON(1+) CATIONIC COMPLEXES

    S SAKAI, H KOZAWA, Y YOSHINAGA, K KOSUGI, S FUKUZAWA, T FUJINAMI

    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS   ( 10 )   663 - 664   1988.5

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  • Samarium(II) Di-iodide Induced Reductive Coupling of α,β-Unsaturated Esters with Carbonyl Compounds Leading to a Facile Synthesis of γ-Lactone Reviewed

    S.Fukuzawa, A.Nakanishi, T.Fujinami, S.Sakai

    J. Chem. Soc., Perkin Trans. I   ( 7 )   1669 - 1674   1988.4

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    DOI: 10.1039/p19880001669

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  • Organic Synthesis Using RLnX(Ln=Lanthanoide)-Type Complexes

    第19回中部化学関係学会協会 支部連合秋季大会 講演予稿集   PB202   346 - 348   1988

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  • REACTION OF ALPHA-HALOGENO KETONES WITH CARBONYL-COMPOUNDS PROMOTED BY CEL3, CECL3-NAL, OR CECL3-SNCL2

    S FUKUZAWA, T TSURUTA, T FUJINAMI, S SAKAI

    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1   ( 7 )   1473 - 1477   1987.7

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    DOI: 10.1039/a901355e

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  • The Nuclepohilic Substitution Reaction Catalyzed by Organotelluronium Salts in Aqueous Media

    T.Takeyama, S.Fukuzawa, T.Fujinami, S.Sakai

    1st. Internat. Sympo. On Hetero Atom Chem.   PS3112   305   1987.7

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  • The Nuclepohilic Substitution Reaction Catalyzed by Organotelluronium Salts in Aqueous Media

    T.Takeyama, S.Fukuzawa, T.Fujinami, S.Sakai

    1st. Internat. Sympo. On Hetero Atom Chem.   PS3112   p.305   1987.7

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  • GENERATION OF A KETOCARBENOID FROM ALPHA,ALPHA-DIBROMODEOXYBENZOIN BY SAMARIUM(II) DIIODIDE AND ITS TRAPPING BY ALKENE CYCLOADDITION

    S FUKUZAWA, T FUJINAMI, S SAKAI

    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS   ( 12 )   919 - 920   1987.6

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  • GENERATION OF A KETOCARBENOID FROM ALPHA,ALPHA-DIBROMODEOXYBENZOIN BY SAMARIUM(II) DIIODIDE AND ITS TRAPPING BY ALKENE CYCLOADDITION

    S FUKUZAWA, T FUJINAMI, S SAKAI

    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS   ( 12 )   919 - 920   1987.6

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    DOI: 10.1039/c39870000919

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  • INTRAMOLECULAR REDUCTIVE CYCLIZATION OF UNSATURATED KETO-ESTERS OR ALDO-ESTERS BY SAMARIUM(II) DIIODIDE - A READY SYNTHESIS OF BICYCLIC GAMMA-LACTONES

    S FUKUZAWA, M IIDA, A NAKANISHI, T FUJINAMI, S SAKAI

    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS   ( 12 )   920 - 921   1987.6

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    DOI: 10.1039/c39870000920

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  • INTRAMOLECULAR REDUCTIVE CYCLIZATION OF UNSATURATED KETO-ESTERS OR ALDO-ESTERS BY SAMARIUM(II) DIIODIDE - A READY SYNTHESIS OF BICYCLIC GAMMA-LACTONES

    S FUKUZAWA, M IIDA, A NAKANISHI, T FUJINAMI, S SAKAI

    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS   ( 12 )   920 - 921   1987.6

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    DOI: 10.1039/c39870000920

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  • Reaction of α-Halogenoketones with Carbonyl Compounds Promoted by Cel3, Cecl3-NaI, or CeCl3-SnCl2 Reviewed

    S.Fukuzawa, T.Tsuruta, T.Fujinami, S.Sakai

    J. Chem. Soc., Perkin Trans. I   ( 7 )   1473 - 1478   1987.4

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    DOI: 10.1039/a901355e

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  • Two-phase Cyclopropanation Reactions of Olefins Using Organo Telluronium Compounds

    第34回有機金属討論会   PB214   379 - 381   1987

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  • DOMINANT CIS-DIACETOXYLATION OF ALKENES WITH TELLURIUM(IV) OXIDE AND LITHIUM BROMIDE IN ACETIC-ACID

    S UEMURA, K OHE, SI FUKUZAWA, PATIL, SR, N SUGITA

    JOURNAL OF ORGANOMETALLIC CHEMISTRY   316 ( 1-2 )   67 - 78   1986.11

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    DOI: 10.1016/0022-328X(86)82076-9

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  • DOMINANT CIS-DIACETOXYLATION OF ALKENES WITH TELLURIUM(IV) OXIDE AND LITHIUM BROMIDE IN ACETIC-ACID

    S UEMURA, K OHE, SI FUKUZAWA, PATIL, SR, N SUGITA

    JOURNAL OF ORGANOMETALLIC CHEMISTRY   316 ( 1-2 )   67 - 78   1986.11

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    DOI: 10.1016/0022-328X(86)82076-9

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  • 1,2-REGIOSELECTIVE REDUCTION OF ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS WITH LITHIUM ALUMINUM-HYDRIDE IN THE PRESENCE OF LANTHANOID SALTS

    S FUKUZAWA, T FUJINAMI, S YAMAUCHI, S SAKAI

    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1   ( 11 )   1929 - 1932   1986.11

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  • 1,2-REGIOSELECTIVE REDUCTION OF ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS WITH LITHIUM ALUMINUM-HYDRIDE IN THE PRESENCE OF LANTHANOID SALTS

    S FUKUZAWA, T FUJINAMI, S YAMAUCHI, S SAKAI

    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1   ( 11 )   1929 - 1932   1986.11

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  • REDUCTIVE COUPLING OF KETONES OR ALDEHYDES WITH ELECTRON-DEFICIENT ALKENES PROMOTED BY SAMARIUM DIIODIDE

    S FUKUZAWA, A NAKANISHI, T FUJINAMI, S SAKAI

    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS   ( 8 )   624 - 625   1986.4

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    DOI: 10.1039/c39860000624

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  • Carbon-Carbon Bond Formation Using Misch Metal Reviewed

    A.Nakanishi, S.Fukuzawa, T.Fujinami, S.Sakai

    Chem. Express   1   275 - 278   1986.4

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  • Carbon-Carbon Bond Formation Using Misch Metal Reviewed

    A.Nakanishi, S.Fukuzawa, T.Fujinami, S.Sakai

    Chem. Express   1   275 - 278   1986.4

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  • REDUCTIVE COUPLING OF KETONES OR ALDEHYDES WITH ELECTRON-DEFICIENT ALKENES PROMOTED BY SAMARIUM DIIODIDE

    S FUKUZAWA, A NAKANISHI, T FUJINAMI, S SAKAI

    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS   ( 8 )   624 - 625   1986.4

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    DOI: 10.1039/c39860000624

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  • A FACILE AND DIRECT SYNTHESIS OF GAMMA-LACTONES FROM METHYL BETA-BROMOPROPIONATE AND KETONES MEDIATED BY LANTHANOID METALS

    S FUKUZAWA, T FUJINAMI, S SAKAI

    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS   ( 6 )   475 - 476   1986.3

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    DOI: 10.1039/c39860000475

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  • A FACILE AND DIRECT SYNTHESIS OF GAMMA-LACTONES FROM METHYL BETA-BROMOPROPIONATE AND KETONES MEDIATED BY LANTHANOID METALS

    S FUKUZAWA, T FUJINAMI, S SAKAI

    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS   ( 6 )   475 - 476   1986.3

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    DOI: 10.1039/c39860000475

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  • ORGANOCERIUM REAGENTS FROM IODINE ACTIVATED CERIUM METAL AND ORGANIC IODIDES - THEIR REACTIONS WITH CARBONYL-COMPOUNDS

    SI FUKUZAWA, T FUJINAMI, S SAKAI

    JOURNAL OF ORGANOMETALLIC CHEMISTRY   299 ( 2 )   179 - 185   1986.1

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    DOI: 10.1016/0022-328X(86)82013-7

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  • ORGANOCERIUM REAGENTS FROM IODINE ACTIVATED CERIUM METAL AND ORGANIC IODIDES - THEIR REACTIONS WITH CARBONYL-COMPOUNDS

    SI FUKUZAWA, T FUJINAMI, S SAKAI

    JOURNAL OF ORGANOMETALLIC CHEMISTRY   299 ( 2 )   179 - 185   1986.1

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    DOI: 10.1016/0022-328X(86)82013-7

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  • Reductive Coupling of Carbonyl Compounds with Electron-deficient Alkenes Promoted by Samarium Di-iodide

    第33回有機金属討論会   B109   163 - 165   1986

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  • Reaction Between α-Halogenoketones and Aldehydes Promoted by Cerium (Ⅲ) Iodide or Cerium(Ⅲ) Chloride-Sodium Iodide

    S.Fukuzawa, T.Fujinami, S.Sasaki

    3rd. IUPAC Sympo. on Organomet. Chem. Directd. Toward Org. Syn.   PS25   1985.7

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  • Application of Oxidative Aryl Migration in Organo-selenium and -tellurium Compounds to the Synthesis of 2-Arylpropanoic Acids Reviewed

    S.Uemura, S.Fukuzawa

    J. Chem. Soc., Perkin Trans.I   1983 - 1987   1985.4

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  • Application of Oxidative Aryl Migration in Organo-selenium and -tellurium Compounds to the Synthesis of 2-Arylpropanoic Acids Reviewed

    S.Uemura, S.Fukuzawa

    J. Chem. Soc., Perkin Trans.I   1983 - 1987   1985.4

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  • Telluroxide Elmination by Direct Oxidation of Alkyl Phenyl Telluride Reviewed

    S.Uemura, K.Ohe, S.Fukuzawa

    Tetrahedron Lett.   26 ( 7 )   895 - 898   1985.4

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    DOI: 10.1016/S0040-4039(00)61958-5

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  • Oxidation of Alkyl Phenyl Selenides, Tellurides, and Telluroxide with m-Chloroperbenzoic Acid for a Facile Transfomation of C-Se and C-Te Bonds to C-O Bonds Reviewed

    S.Uemura, S.Fukuzawa

    J. Chem. Soc. Perkin Trans. I   471 - 490   1985.4

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  • TELLUROXIDE ELIMINATION BY DIRECT OXIDATION OF ALKYL PHENYL TELLURIDE

    S UEMURA, K OHE, S FUKUZAWA

    TETRAHEDRON LETTERS   26 ( 7 )   895 - 898   1985

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    DOI: 10.1016/S0040-4039(00)61958-5

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  • ALLYLIC ALCOHOLS FORMATION BY OXIDATION OF ALLYLIC PHENYL TELLURIDES - A POSSIBLE [2,3]SIGMATROPIC REARRANGEMENT OF ALLYLIC TELLUROXIDES

    S UEMURA, S FUKUZAWA, K OHE

    TETRAHEDRON LETTERS   26 ( 7 )   921 - 924   1985

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    DOI: 10.1016/S0040-4039(00)61965-2

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  • ALLYLIC ALCOHOLS FORMATION BY OXIDATION OF ALLYLIC PHENYL TELLURIDES - A POSSIBLE [2,3]SIGMATROPIC REARRANGEMENT OF ALLYLIC TELLUROXIDES

    S UEMURA, S FUKUZAWA, K OHE

    TETRAHEDRON LETTERS   26 ( 7 )   921 - 924   1985

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    DOI: 10.1016/S0040-4039(00)61965-2

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  • LIQUID-PHASE 1,4-DIACETOXYLATION OF CONJUGATED DIENES WITH TELLURIUM(IV) OXIDE AND ALKALI-METAL HALIDES

    S UEMURA, SI FUKUZAWA, PATIL, SR, M OKANO

    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1   ( 3 )   499 - 503   1985

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  • Reaction Between α-Halogenoketones and Aldehydes Promoted by Cerium (Ⅲ) Iodide or Cerium(Ⅲ) Chloride-Sodium Iodide

    3rd. IUPAC Sympo. on Organomet. Chem. Directd. Toward Org. Syn.   PS25   1985

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  • LIQUID-PHASE 1,4-DIACETOXYLATION OF CONJUGATED DIENES WITH TELLURIUM(IV) OXIDE AND ALKALI-METAL HALIDES

    S UEMURA, SI FUKUZAWA, PATIL, SR, M OKANO

    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1   ( 3 )   499 - 503   1985

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  • OXIDATION OF ALKYL PHENYL SELENIDES, TELLURIDES, AND TELLUROXIDES WITH META-CHLOROPERBENZOIC ACID FOR A FACILE AND NOVEL TRANSFORMATION OF C-SE AND C-TE BONDS TO C-O BONDS

    S UEMURA, SI FUKUZAWA

    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1   ( 3 )   471 - 480   1985

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  • CARBON-CARBON BOND FORMATION BETWEEN ALPHA-HALOGENOKETONES AND ALDEHYDES PROMOTED BY CERIUM(III) IODIDE OR CERIUM(III) CHLORIDE-SODIUM IODIDE

    S FUKUZAWA, T FUJINAMI, S SAKAI

    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS   ( 12 )   777 - 778   1985

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    DOI: 10.1039/c39850000777

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  • PALLADIUM CATALYZED REACTION OF BUTADIENE MONOXIDE WITH CARBON-DIOXIDE

    T FUJINAMI, T SUZUKI, M KAMIYA, S FUKUZAWA, S SAKAI

    CHEMISTRY LETTERS   ( 2 )   199 - 200   1985

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    DOI: 10.1246/cl.1985.199

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  • PALLADIUM CATALYZED REACTION OF BUTADIENE MONOXIDE WITH CARBON-DIOXIDE

    T FUJINAMI, T SUZUKI, M KAMIYA, S FUKUZAWA, S SAKAI

    CHEMISTRY LETTERS   ( 2 )   199 - 200   1985

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    DOI: 10.1246/cl.1985.199

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  • CARBON-CARBON BOND FORMATION BETWEEN ALPHA-HALOGENOKETONES AND ALDEHYDES PROMOTED BY CERIUM(III) IODIDE OR CERIUM(III) CHLORIDE-SODIUM IODIDE

    S FUKUZAWA, T FUJINAMI, S SAKAI

    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS   ( 12 )   777 - 778   1985

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    DOI: 10.1039/c39850000777

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  • NEW PREPARATIVE METHOD FOR 2-ARYLPROPANOIC ACIDS BY OXIDATIVE ARYL MIGRATION IN ARYL ALPHA-SELENO-ETHYL AND ARYL ALPHA-TELLURO-ETHYL KETONES

    S UEMURA, S FUKUZAWA, T YAMAUCHI, K HATTORI, S MIZUTAKI, K TAMAKI

    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS   ( 7 )   426 - 427   1984

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    DOI: 10.1039/c39840000426

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  • ALPHA-ELIMINATION OF ORGANIC HALIDES FROM ORGANOTELLURIUM(IV) HALIDES

    S UEMURA, SI FUKUZAWA

    JOURNAL OF ORGANOMETALLIC CHEMISTRY   268 ( 3 )   223 - 234   1984

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    DOI: 10.1016/0022-328X(84)80257-0

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  • ALPHA-ELIMINATION OF ORGANIC HALIDES FROM ORGANOTELLURIUM(IV) HALIDES

    S UEMURA, SI FUKUZAWA

    JOURNAL OF ORGANOMETALLIC CHEMISTRY   268 ( 3 )   223 - 234   1984

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    DOI: 10.1016/0022-328X(84)80257-0

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  • NEW PREPARATIVE METHOD FOR 2-ARYLPROPANOIC ACIDS BY OXIDATIVE ARYL MIGRATION IN ARYL ALPHA-SELENO-ETHYL AND ARYL ALPHA-TELLURO-ETHYL KETONES

    S UEMURA, S FUKUZAWA, T YAMAUCHI, K HATTORI, S MIZUTAKI, K TAMAKI

    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS   ( 7 )   426 - 427   1984

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    DOI: 10.1039/c39840000426

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  • NEW ASPECTS OF THE TELLUROXIDE ELIMINATION - A FACILE ELIMINATION OF SEC-ALKYL PHENYL TELLUROXIDE LEADING TO OLEFINS, ALLYLIC ALCOHOLS, AND ALLYLIC ETHERS

    S UEMURA, S FUKUZAWA

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   105 ( 9 )   2748 - 2752   1983

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    DOI: 10.1021/ja00347a039

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  • A NOVEL, SIMPLE METHOD FOR TRANSFORMATION OF C-SE TO C-O BONDS

    S UEMURA, S FUKUZAWA, A TOSHIMITSU

    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS   ( 24 )   1501 - 1502   1983

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    DOI: 10.1039/c39830001501

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  • A NOVEL, SIMPLE METHOD FOR TRANSFORMATION OF C-SE TO C-O BONDS

    S UEMURA, S FUKUZAWA, A TOSHIMITSU

    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS   ( 24 )   1501 - 1502   1983

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    DOI: 10.1039/c39830001501

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  • NEW ASPECTS OF THE TELLUROXIDE ELIMINATION - A FACILE ELIMINATION OF SEC-ALKYL PHENYL TELLUROXIDE LEADING TO OLEFINS, ALLYLIC ALCOHOLS, AND ALLYLIC ETHERS

    S UEMURA, S FUKUZAWA

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   105 ( 9 )   2748 - 2752   1983

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    DOI: 10.1021/ja00347a039

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  • PHOSPHINE-NICKEL(II), PHOSPHINE-COBALT(II), PHOSPHINE-PALLADIUM(0) AND PHOSPHINE-PALLADIUM(II) COMPLEXES AS CATALYSTS IN CROSS-COUPLING REACTIONS OF ARYL-GRIGNARD AND ALKYL-GRIGNARD REAGENTS WITH ORGANIC TELLURIDES

    S UEMURA, SI FUKUZAWA, PATIL, SR

    JOURNAL OF ORGANOMETALLIC CHEMISTRY   243 ( 1 )   9 - 18   1983

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    Language:English   Publisher:ELSEVIER SCIENCE SA LAUSANNE  

    DOI: 10.1016/0022-328X(83)80215-0

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  • NOVEL OXIDATION OF ALKYL PHENYL TELLURIDES AND TELLUROXIDES WITH META-CHLOROPERBENZOIC ACID - REPLACEMENT OF TELLURIUM MOIETY BY METHOXY GROUP ACCOMPANIED BY RING-CONTRACTION AND PHENYL MIGRATION

    S UEMURA, S FUKUZAWA

    TETRAHEDRON LETTERS   24 ( 40 )   4347 - 4350   1983

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    Language:English   Publisher:PERGAMON-ELSEVIER SCIENCE LTD  

    DOI: 10.1016/S0040-4039(00)88338-0

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  • NOVEL OXIDATION OF ALKYL PHENYL TELLURIDES AND TELLUROXIDES WITH META-CHLOROPERBENZOIC ACID - REPLACEMENT OF TELLURIUM MOIETY BY METHOXY GROUP ACCOMPANIED BY RING-CONTRACTION AND PHENYL MIGRATION

    S UEMURA, S FUKUZAWA

    TETRAHEDRON LETTERS   24 ( 40 )   4347 - 4350   1983

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    DOI: 10.1016/S0040-4039(00)88338-0

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  • OXYTELLURATION OF OLEFINS TO (BETA-ALKOXY- AND BETA-HYDROXY-ALKYL)ARYLTELLURIUM DIHALIDES AND THEIR REACTIONS WITH REDUCING AGENTS AND AQUEOUS NAOH

    S UEMURA, SI FUKUZAWA, A TOSHIMITSU

    JOURNAL OF ORGANOMETALLIC CHEMISTRY   250 ( 1 )   203 - 215   1983

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    DOI: 10.1016/0022-328X(83)85051-7

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  • OXYTELLURATION OF OLEFINS TO (BETA-ALKOXY- AND BETA-HYDROXY-ALKYL)ARYLTELLURIUM DIHALIDES AND THEIR REACTIONS WITH REDUCING AGENTS AND AQUEOUS NAOH

    S UEMURA, SI FUKUZAWA, A TOSHIMITSU

    JOURNAL OF ORGANOMETALLIC CHEMISTRY   250 ( 1 )   203 - 215   1983

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    DOI: 10.1016/0022-328X(83)85051-7

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  • PHOSPHINE-NICKEL(II), PHOSPHINE-COBALT(II), PHOSPHINE-PALLADIUM(0) AND PHOSPHINE-PALLADIUM(II) COMPLEXES AS CATALYSTS IN CROSS-COUPLING REACTIONS OF ARYL-GRIGNARD AND ALKYL-GRIGNARD REAGENTS WITH ORGANIC TELLURIDES

    S UEMURA, SI FUKUZAWA, PATIL, SR

    JOURNAL OF ORGANOMETALLIC CHEMISTRY   243 ( 1 )   9 - 18   1983

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    DOI: 10.1016/0022-328X(83)80215-0

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  • PALLADIUM-CATALYZED ALLYLIC OXIDATION OF OLEFINS BY TERT-BUTYL HYDROPEROXIDE AND TELLURIUM(IV) OXIDE

    S UEMURA, S FUKUZAWA, A TOSHIMITSU, M OKANO

    TETRAHEDRON LETTERS   23 ( 1 )   87 - 90   1982

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    DOI: 10.1016/S0040-4039(00)97540-3

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  • NI(II)PHOSPHINE AND CO(II)-PHOSPHINE COMPLEX CATALYZED CARBON-CARBON BOND FORMATION BETWEEN ORGANIC TELLURIDES AND GRIGNARD-REAGENTS

    S UEMURA, S FUKUZAWA

    TETRAHEDRON LETTERS   23 ( 11 )   1181 - 1184   1982

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    DOI: 10.1016/S0040-4039(00)87054-9

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  • NI(II)PHOSPHINE AND CO(II)-PHOSPHINE COMPLEX CATALYZED CARBON-CARBON BOND FORMATION BETWEEN ORGANIC TELLURIDES AND GRIGNARD-REAGENTS

    S UEMURA, S FUKUZAWA

    TETRAHEDRON LETTERS   23 ( 11 )   1181 - 1184   1982

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    DOI: 10.1016/S0040-4039(00)87054-9

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  • A FACILE METHOD FOR OXYTELLURATION OF OLEFINS

    S UEMURA, S FUKUZAWA, A TOSHIMITSU, M OKANO

    TETRAHEDRON LETTERS   23 ( 11 )   1177 - 1180   1982

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    DOI: 10.1016/S0040-4039(00)87053-7

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  • A FACILE METHOD FOR OXYTELLURATION OF OLEFINS

    S UEMURA, S FUKUZAWA, A TOSHIMITSU, M OKANO

    TETRAHEDRON LETTERS   23 ( 11 )   1177 - 1180   1982

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    DOI: 10.1016/S0040-4039(00)87053-7

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  • PALLADIUM-CATALYZED ALLYLIC OXIDATION OF OLEFINS BY TERT-BUTYL HYDROPEROXIDE AND TELLURIUM(IV) OXIDE

    S UEMURA, S FUKUZAWA, A TOSHIMITSU, M OKANO

    TETRAHEDRON LETTERS   23 ( 1 )   87 - 90   1982

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    DOI: 10.1016/S0040-4039(00)97540-3

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  • HALOGENODETELLURATION OF ARYLTELLURIUM(IV) COMPOUNDS

    S UEMURA, SI FUKUZAWA, M WAKASUGI, M OKANO

    JOURNAL OF ORGANOMETALLIC CHEMISTRY   214 ( 3 )   319 - 324   1981

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    DOI: 10.1016/S0022-328X(81)80006-X

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  • SELECTIVE 1,4-DIACETOXYLATION OF CONJUGATED DIENES WITH TELLURIUM(IV) OXIDE

    S UEMURA, SI FUKUZAWA, M OKANO

    TETRAHEDRON LETTERS   22 ( 52 )   5331 - 5334   1981

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    DOI: 10.1016/S0040-4039(01)92494-3

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  • SELECTIVE 1,4-DIACETOXYLATION OF CONJUGATED DIENES WITH TELLURIUM(IV) OXIDE

    S UEMURA, SI FUKUZAWA, M OKANO

    TETRAHEDRON LETTERS   22 ( 52 )   5331 - 5334   1981

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    DOI: 10.1016/S0040-4039(01)92494-3

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  • HALOGENODETELLURATION OF ARYLTELLURIUM(IV) COMPOUNDS

    S UEMURA, SI FUKUZAWA, M WAKASUGI, M OKANO

    JOURNAL OF ORGANOMETALLIC CHEMISTRY   214 ( 3 )   319 - 324   1981

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    DOI: 10.1016/S0022-328X(81)80006-X

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  • THE CHLOROIODINATION OF DEACTIVATED OLEFINS WITH ANTIMONY(V) CHLORIDE-IODINE AND IODINE MONOCHLORIDE

    S UEMURA, S FUKUZAWA, M OKANO, S SAWADA

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   53 ( 5 )   1390 - 1392   1980

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  • PEROXIDE-INDUCED ALPHA-ELIMINATION OF ORGANIC HALIDES FROM ORGANOTELLURIUM(IV) HALIDES

    S UEMURA, S FUKUZAWA

    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS   ( 21 )   1033 - 1034   1980

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  • Photolytic α-Elimination of Organic Halides From Organotellurium(Ⅳ) Halides

    Sakae Uemura, Shin-ichi Fukuzawa

    Chem. Lett.   ( 8 )   943 - 946   1980

  • PHOTOLYTIC ALPHA-ELIMINATION OF ORGANIC HALIDES FROM ORGANOTELLURIUM(IV) HALIDES

    S UEMURA, S FUKUZAWA

    CHEMISTRY LETTERS   ( 8 )   943 - 946   1980

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    DOI: 10.1246/cl.1980.943

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  • THE CHLOROIODINATION OF DEACTIVATED OLEFINS WITH ANTIMONY(V) CHLORIDE-IODINE AND IODINE MONOCHLORIDE

    S UEMURA, S FUKUZAWA, M OKANO, S SAWADA

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   53 ( 5 )   1390 - 1392   1980

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    DOI: 10.1246/bcsj.53.1390

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  • PEROXIDE-INDUCED ALPHA-ELIMINATION OF ORGANIC HALIDES FROM ORGANOTELLURIUM(IV) HALIDES

    S UEMURA, S FUKUZAWA

    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS   ( 21 )   1033 - 1034   1980

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    DOI: 10.1039/c39800001033

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Presentations

  • キラル銀錯体触媒を用いるイミノラクトンとイリデン-イソオキサゾロンとのendo'-選択的不斉[3+2]環化付加反応

    古屋 翔平, 室井 賢二, 福澤 信一

    日本化学会第103回春季年会  2023.3 

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  • キラル銅錯体触媒を用いるイミノエステルとシアノスルホンとのexo選択的不斉1,3-双極子環化付加反応

    佐久間 夕季, 古屋 翔平, 福澤 信一

    日本化学会第103回春季年会  2023.3 

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  • キラル銅錯体触媒を用いるイミノラクトンとアルキリデンピラゾロンとのendo’-選択的不斉[3+2]環化付加反応

    室井 賢二, 古屋 翔平, 福澤 信一

    日本化学会第103回春季年会  2023.3 

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  • 新規フェロセニルオキサゾリンスルホキシド配位子の合成とその性能評価

    齋藤 一輝, 福澤 信一

    第12回CSJ化学フェスタ2022  2022.10 

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    Event date: 2022.10    

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  • 軸不斉を有する新規キラルフェロセニルホスフィン配位子の合成と不斉有機合成反応への応用

    清水 駿吾, 大澤 一輝, 福澤 信一

    第12回CSJ化学フェスタ2022  2022.10 

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  • 不斉 1,3-双極子環化付加反応を用いるスピロピロリジンの 2,5-trans 選択的合成

    古屋翔平, 井上綾菜, 福澤信一

    第51回複素環化学討論会  2022.9 

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    Event date: 2022.9    

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  • 金属錯体触媒を用いるイミノエステルとイリデン ヘテロ環化合物との2,5-trans選択的不斉[3+2]環化付加 反応

    古屋 翔平, 井上 綾菜, 福澤 信ー

    第68回有機金属化学討論会  2022.9 

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  • キラルビナフチル基の導入によるキラルフェロセ ニルホスフィン配位子とその金属錯体の合成

    清水 駿吾, 坂井 傑, 大澤 一輝, 福澤 信一

    第68回有機金属化学討論会  2022.9 

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  • SYNTHESIS OF NOVEL PLANAR CHIRAL MONOPHOSPHINE LIGANDS BEARING FERROCENYL-TRIAZOLE BACKBONES AND THEIR USE IN ASYMMETRIC CROSS-COUPLING REACTION

    Suguru Sakai, Shin-ichi Fukuzawa

    29th International Conference on Organometallic Chemistry  2022.7 

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    Event date: 2022.7    

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  • EXOʹ-SELECTIVE CONSTRUCTION OF SPIROBIPYRROLIDINES BY THE SILVER-CATALYZED ASYMMETRIC [3+2] CYCLOADDITION OF IMINO ESTERS WITH 2,3-DIOXOPYRROLIDINES

    Shohei Furuya, Ayana Inoue, Shin-ichi Fukuzawa

    29th International Conference on Organometallic Chemistry  2022.7 

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  • 光学活性2-ビナフトイルフェロセンの還元と キラルフェロセニルホスフィン配位子の合成

    清水 駿吾, 坂井傑, 福澤信一

    第82回有機合成化学協会関東支部シンポジウム  2022.5 

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  • イミド基を脱離基とするジスルフィド構造へのアミン導入反応

    浅沼 隼人, 金本 和也, 福澤 信一

    日本化学会第102春季年会  ( 関西学院大学 )   2022.3  日本化学会

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  • 硫黄原子上に配置したイミド基を脱離基とするアズラクトンのジスルフィド化反応

    細野 兼矢, 浅沼 隼人, 金本 和也, 福澤 信一

    日本化学会第102春季年会  ( 関西学院大学 )   2022.3  日本化学会

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  • 銀触媒を用いるイミノエステルとデヒドロアラニンの1,3-双極子環化付加反応

    岩田 真輝, 町田 陽佳, 金本 和也, 福澤 信一

    日本化学会第102春季年会  ( 関西学院大学 )   2022.3  日本化学会

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  • 銀錯体触媒系を用いたイミノニトリルのα,β-不飽和ケトンへの不斉Michael付加反応

    荒城 春奈, 金本 和也, 福澤 信一

    日本化学会第102春季年会  ( 関西学院大学 )   2022.3  日本化学会

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  • キラル銀錯体触媒を用いるイミノエステルと2,3-ジオキソピロリジンとのexo'-選択的不斉[3+2]環化付加反応

    古屋翔平, 金本和也, 福澤信一

    第81回有機合成化学協会関東支部シンポジウム  ( 群馬大学 )   2021.11  有機合成化学協会関東支部

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  • 銀/ThioClickFerrophos錯体触媒を用いた環状イミノニトリルとエノンの不斉Michael付加反応

    荒城春奈, 金本和也, 福澤信一

    第81回有機合成化学協会関東支部シンポジウム  ( 群馬大学 )   2021.11  有機合成化学協会関東支部

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  • 脱離基の選択的な変換が可能なジスルフィドプラットフォームの開発

    浅沼隼人, 金本和也, 渡邊時春, 福澤信一

    第81回有機合成化学協会関東支部シンポジウム  ( 群馬大学 )   2021.11  有機合成化学協会関東支部

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  • ペプチドのN末端修飾を志向した1,3-双極子環化付加反応

    町田陽佳, 金本和也, 福澤信一

    第119回有機合成シンポジウム  ( 早稲田大学 )   2021.11  有機合成化学協会

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  • 1,3-双極子環化付加反応を用いた強固な結合形成を伴うペプチドのN末端修飾法の開発

    町田 陽佳, 金本 和也, 福澤 信一

    第11回化学フェスタ  ( 東京 )   2021.10  日本化学会

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  • アミド基とイミド基の脱離能の違いを利用したジスルフィドプラットフォーム分子の開発

    浅沼 隼人, 金本 和也, 渡邉 時春, 福澤 信一

    第11回化学フェスタ  ( 東京 )   2021.10  日本化学会

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  • 銀触媒錯体を用いた環状イミノニトリルのエノンへの 立体選択的Michael付加反応

    荒城 春奈, 福澤 信一, 金本 和也

    第11回化学フェスタ  ( 東京 )   2021.10  日本化学会

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  • 新規光学活性ビアリールホスフィン配位子の合成とその性能評価

    坂井 傑, 金本 和也, 福澤 信一

    第11回化学フェスタ  ( 東京 )   2021.10  日本化学会

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  • 銀触媒を用いた MBH 付加物とアゾメチンイリドの不斉 1,3-双極子環化付加反応とタンデム型付加-脱離反応

    井上綾菜, 金本和也, 福澤信一

    第50回複素環化学討論会  ( 静岡県立大学 )   2021.10  複素環化学討論会実行委員会

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  • キラル金属錯体触媒を用いる 2-ピロリンエステルと 2-ニトロ酢酸アリルとの不斉付加-脱離反応

    大野壱樹, 古屋翔平, 金本和也, 福澤信一

    第50回複素環化学討論会  ( 静岡県立大学 )   2021.10  複素環化学討論会実行委員会

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  • 新規面不斉フェロセン型モノホスフィン配位子の合成とその性能評価

    坂井傑, 金本和也, 福澤信一

    第79回有機合成化学協会関東支部シンポジウム  ( 東工大大岡山キャンパス )   2021.5  有機合成化学協会関東支部

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  • ハロゲン結合供与型触媒によるアルデヒドのシリルシアノ化反応

    西尾和優, 鳥田康樹, 原口亮介, 福沢信一

    第79回有機合成化学協会関東支部シンポジウム  ( 東工大大岡山キャンパス )   2021.5  有機合成化学協会関東支

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  • 硫黄原子上の脱離基を選択的に変換する非対称ジスルフィド合成法の開発

    渡邉時春, 浅沼隼人, 金本和也, 福澤信一

    第79回有機合成化学協会関東支部シンポジウム  ( 東工大大岡山キャンパス )   2021.5  有機合成化学協会関東支部

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  • 銀/ThioClickFerrophos錯体触媒を用いたMorita–Baylis–Hillman付加体とアゾメチンイリドの不斉付加反応

    井上綾菜, 鈴木裕子, 金本和也, 福澤信一

    第79回有機合成化学協会関東支部シンポジウム  ( 東工大大岡山キャンパス )   2021.5  有機合成化学協会関東支部

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  • イミノペプチドを用いた1,3-双極子環化付加反応によるペプチドのN末端修飾

    町田陽佳, 金本和也, 福澤信一

    第79回有機合成化学協会関東支部シンポジウム  ( 東工大大岡山キャンパス )   2021.5  有機合成化学協会関東支部

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  • 銅・銀塩複合触媒系を用いるN-キノリルアミドフェロセンのC-Hアミノ化反応

    堀川渚生, 金本和也, 福澤信一

    第79回有機合成化学協会関東支部シンポジウム  ( 東工大大岡山キャンパス )   2021.5  有機合成化学協会関東支部

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  • Development of Bulky Planar Chiral Triazolylidene Metal Complexes

    伊藤 樹生, 鳥田 康樹, 金本 和也, 原口 亮介, 福澤 信一

    第101回日本化学会春季年会  ( オンライン )   2021.3  日本化学会

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  • Silver/ThioClickFerrophos Complex-Catalyzed exo’-Selective Asymmetric [3+2] Cycloaddition of Iminoesters with 2,3-Dioxopyrrolidines

    古屋 翔平, 金本 和也, 福澤 信一

    第101回日本化学会春季年会  ( オンライン )   2021.3  日本化学会

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  • Ag/ThioClickFerrophos Complex Catalyzed Asymmetric 1,3-Dipolar Cycloaddition of Imino Esters to Morita– Baylis– Hillman Adducts

    井上 綾菜, 金本 和也, 福澤 信一

    第101回日本化学会春季年会  ( オンライン )   2021.3  日本化学会

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  • N-Terminal Peptide Modification by Cu(I)-Catalyzed 1,3-Dipolar Cycloaddition

    町田 陽佳, 金本 和也, 福澤 信一

    第101回日本化学会春季年会  ( オンライン )   2021.3  日本化学会

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  • Synthesis of Unsymmetrical Disulfides by Selective Conversion of Sulfur-bonded Amino and Imide Groups

    浅沼 隼人, 渡邉 時春, 金本 和也, 福澤 信一

    第101回日本化学会春季年会  ( オンライン )   2021.3  日本化学会

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  • Sulfonylthiolation of Arenes via Selective Activation of SS–morpholino dithiosulfonate

    金本 和也, 古橋 昂大, 渡邉 時春, 浅沼 隼人, 福澤 信一

    第101回日本化学会春季年会  ( オンライン )   2021.3  日本化学会

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  • 銅・銀触媒系を用いるN-キノリルフェロセニルアミドのC-Hアミノ化反応

    堀川渚生, 金本和也, 福澤信一

    第10回CSJ化学フェスタ2020  ( 東京 )   2020.10  日本化学会

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  • キラル銀錯体触媒を用いる2-ピロリンエステルの2-ニトロ酢酸アリルへの不斉付加-脱離反応

    大野 壱樹, 古屋 翔平, 金本 和也, 福澤 信一

    第10回CSJ化学フェスタ2020  ( 東京 )   2020.10  日本化学会

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  • カリウムチオスルホナートを用いたα,β-不飽和カルボニル化合物のスルホニル化反応の開発

    渡邉 時春, 古橋 昂大, 鳥田 康樹, 金本 和也, 福澤 信一

    第10回CSJ化学フェスタ2020  ( 東京 )   2020.10  日本化学会

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  • 銀錯体触媒を用いるピロリンエステルのMorita-Baylis-Hillman 付加体への立体選択的付加反応

    鈴木裕子, 大野壱樹, 金本和也, 福澤信一

    第100回日本化学会春季年会  ( 東京理科大学野田キャンパス )   2020.3  日本化学会

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  • 銀錯体触媒を用いるピロリンエステルの三置換オレフィンへの Michael 付加反応による立体選択的連続四置換炭素構築法

    加藤萩真, 鈴木裕子, 金本和也, 福澤信一

    第100回日本化学会春季年会  ( 東京理科大学野田キャンパス )   2020.3  日本化学会

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  • カリウムチオスルホナートを用いる活性オレフィンのチオスル ホニル化反応の開発

    渡邉時春, 金本和也, 古橋昂大, 鳥田康樹, 福澤信一

    第100回日本化学会春季年会  ( 東京理科大学野田キャンパス )   2020.3  日本化学会

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  • 銅触媒を用いるアミド置換フェロセンのC-H アミノ化反応

    堀川渚生, 鈴木航太, 金本和也, 福澤信一

    第100回日本化学会春季年会  ( 東京理科大学野田キャンパス )   2020.3  日本化学会

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  • 銀錯体触媒を用いるピロリンエステルのニトロアリルアセテー トへの立体選択的付加反応

    大野壱樹, 鈴木裕子, 加藤萩真, 金本和也, 福澤信一

    第100回日本化学会春季年会  ( 東京理科大学野田キャンパス )   2020.3  日本化学会

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  • 不斉1,3-双極子環化付加反応を用いるスルトン-ピロリジン縮 環化合物の合成

    古屋翔平, 加藤萩真, 金本和也, 福, 澤信一

    第100回日本化学会春季年会  ( 東京理科大学野田キャンパス )   2020.3  日本化学会

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  • Enantio- and Diastereoselective Construction of Two Quaternary Stereogenic Center in Silver-catalyzed Conjugate Addition of 1-Pyrroline Carboxylate to Trisubstituted Nitroalkenes International conference

    Yuko Suzuki, Shuma Kato, Kazuya Kanemoto, Shin-ichi Fukuzawa

    The 18th Asian Chemical Congress  ( Taipei, Taiwan )   2019.12  Organizing Committee of The 18th Asian Chemical Congress

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  • Synthesis of Boc-Protected Ethynyl-Substituted Indigos as Precursors of Functional Indigos International conference

    Satoshi Kemmochi, Shin-ichi Fukuzawa

    The 18th Asian Chemical Congress  ( Taipei, Taiwan )   2019.12  Organizing Committee of The 18th Asian Chemical Congress

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  • Metal-catalyzed Enantioselective 1,3-Dipolar Cycloaddition of Azomethine Ylides with 1-Propene-1,3-Sultone: Syntesis of Bicyclic Sultone-fused Pyrrolidines International conference

    Shohei Furuya, Shin-ichi Fukuzawa

    The 18th Asian Chemical Congress  ( Taipei, Taiwan )   2019.12  Organizing Committee of The 18th Asian Chemical Congress

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  • キラル金属錯体触媒を用いたピロリンエステルと3置換アルケンとの不斉Michael付加反応の開発

    加藤萩真, 鈴木裕子, 金本和也, 福澤信一

    第9回化学フェスタ  ( タワーホール船堀 )   2019.10  日本化学会

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  • キラル金属錯体触媒を用いたオキサゾリンエステルとアルケニルイソオキサゾールの不斉Michael付加反応

    鈴木裕子, 加藤萩真, 金本和也, 福澤信一

    第9回化学フェスタ  ( タワーホール船堀 )   2019.10  日本化学会

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  • アゾメチンイリドとスルトンとの触媒的不斉1,3-双極子環化付加反応

    古屋翔平, 加藤萩真, 大野壱樹, 金本和也, 福澤信一

    第9回化学フェスタ  ( タワーホール船堀 )   2019.10  日本化学会

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  • チオスルホン酸塩を用いるMichael付加反応によるチオスルホナート合成法の開発

    古橋昂大, 鳥田康樹, 渡邉時春, 金本和也, 福澤信一

    第9回化学フェスタ  ( タワーホール船堀 )   2019.10  日本化学会

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  • 二点活性化型ハロゲン結合供与体による単純アルデヒドの触媒的シリルシアノ化反応

    鳥田康樹, 原口亮介, 金本和也, 福澤信一

    第9回化学フェスタ  ( タワーホール船堀 )   2019.10  日本化学会

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  • キラル同触媒を用いるアゾメチンイリドとスルトンとの不斉1,3−双極子環化付加反応

    古屋翔平, 加藤萩真, 金本和也, 福澤信一

    第66回有機金属化学討論会  ( 首都大学東京南大沢キャンパス )   2019.9  近畿化学協会

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  • 面不斉フェロセンを有するキラルトリアゾーリリデンCu錯体触媒の開発

    山崎達郎, 原口良介, 金本和也, 福澤信一

    第66回有機金属化学討論会  ( 首都大学東京南大沢キャンパス )   2019.9  近畿化学協会

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  • 銀錯体触媒を用いる環状アゾメチンイリドとニトロ活性アルケンとのマイケル付加反応

    鈴木裕子, 加藤萩真, 金本和也, 福澤信一

    第66回有機金属化学討論会  ( 首都大学東京南大沢キャンパス )   2019.9  近畿化学協会

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  • Copper-Catalyzed Asymmetric 1,3-Dipolar Cycloaddition of Glycine Imino Esters with 1-Propene-1,3-Sultone International conference

    Shohei Furuya, Shuma, Kato, Kazuya, Kanemoto, Shin-ichi Fukuzawa

    20th IUPAC Symposium on Organometallic Chemistry Directed Towards Organic Synthesis  ( Heidelberg, Germany )   2019.7  IUPAC

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  • Chiral Metal Complex-Catalyzed Stereoselective Addition Reaction of Trisubstituted Nitroalkenes to Pyrroline Esters International conference

    Shuma Kato, Yuko Suzuki, Kazuya Kanemoto, Shin-ichi Fukuzawa

    20th IUPAC Symposium on Organometallic Chemistry Directed Towards Organic Synthesis  ( Heidelberg, Germany )   2019.7  IUPAC

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  • Silver-Catalyzed 1,3-Dipolar Cycloaddition Reaction of Glycine Imino Esters with Allyl Nitroacetate International conference

    Kouta Suzuki, Shin-ichi Fukuzawa

    23rd Conference on Organometallic Chemistry  ( Helsinki, Finland )   2019.6  Organizing Committee of EUCOMC

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  • Development of Chiral Triazolylidene Cu(II) Complex Catalyst with Ferrocene-based Planar Chirality International conference

    Tatsuro Yamazaki, Ryosuke Haraguchi, Kazuya Kanemoto, Shin-ichi Fukuzawa

    23rd Conference on Organometallic Chemistry  ( Helsinki, Finland )   2019.6  Organizing Committee of EUCOMC

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  • 銀錯体触媒を用いたグリシンイミノエステルとニトロ酢酸アリルとの立体選択的1,3-双極子環化付加反応

    鈴木航太, 原口亮介, 福澤信一

    第77回有機合成化学協会関東支部シンポジウム  ( 慶應義塾大学,矢上キャンパス )   2019.5  有機合成化学協会関東支部

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  • 二点活性化型ハロゲン結合供与型触媒によるアルデヒドのシリルシアノ化反応

    原口亮介, 鳥田康樹, 剱持智志, 福澤信一

    第77回有機合成化学協会関東支部シンポジウム  ( 慶應義塾大学矢上キャンパス )   2019.5  有機合成化学協会関東支部

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  • 銅触媒系でのイミノエステルとスルトンとの立体選択的1,3-双極子環化付加反応

    加藤萩真, 古屋翔平, 原口亮介, 福澤信一

    第77回有機合成化学協会関東支部シンポジウム  ( 慶應義塾大学矢上キャンパス )   2019.5  有機合成化学協会関東支部

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  • カルボニル基を有するヨードトリアゾリウム塩の合成法の開発と触媒機能評価

    剱持智志, 原口亮介, 福澤信一

    第77回有機合成化学協会関東支部シンポジウム  ( 慶應義塾大学矢上キャンパス )   2019.5  有機合成化学協会関東支部

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  • 銅塩を用いたアゾメチンイリドとスルトンとの立体選択的1,3-双極子感化付加反応

    古屋翔平, 原口亮介, 福澤信一

    日本化学会第99春季年会  ( 神戸 )   2019.3 

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  • 面不斉フェロセンを有するキラルトリアゾリリデンCu錯体触媒の開発

    山崎達郎, 原口亮介, 福澤信一

    日本化学回第99春季年会  ( 神戸 )   2019.3 

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  • ハロゲン結合供与型触媒によるアルデヒドのシリルシアノ化反応

    鳥田康樹, 原口亮介, 福澤信

    日本化学会第99春季年会  ( 神戸 )   2019.3 

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  • 触媒活性点周辺の空間制御に基づく高活性ハロゲン結合供与型触媒の創製

    原口亮介, 星野舜, 酒井志徳, 棚沢翔吾, 平石陽一, 遠藤幸四郎, 鳥田康樹, 剣持智, 阿保隼人, 福澤信一

    第76回有機合成化学協会関東支部シンポジウム  ( 長岡 )   2018.12 

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  • Regio- and Stereodivergent Synthesis of Fused Sulfolanes by Asymmetric 1,3-Dipolar Cycloaddition International conference

    Shuma Kato, Masato Harada, Shin-ichi Fukuzawa

    13th International Symposium on Organic reactions  ( Shichu, taipei )   2018.11 

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  • Silver/ThioClickFerrophos-catalyzed Asymmetric Michael Addition of 1-Pyrroline-5-Carboxylates to 3-Methyl-5-nitro-5-styrylisoxazoles International conference

    Shuma Kato, Shin-ichi Fukuzawa

    22nd International Conference on Organic Synthesis  ( Florence, Italy )   2018.9  Organizing Committee of 22-ICOS

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  • Synthesis and Application of Chiral Ferrocenyl-based Mesoionic 1,2,3-Triazolylidene Palladium Complexes International conference

    Tatsuro Yamazaki, Ryosuke Haraguchia, Shin-ichi Fukuzawa

    22nd International Conference on Organic Synthesis  ( Florence, Italy )   2018.9  Organizing Committee of 22-ICOS

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  • 銀/ThioClickFerrophosを用いたピロリンエステルとアルケニルイソオキサゾールとの不斉Micheal付加反応

    加藤萩真, 福澤信一, 原口亮介

    日本化学会第98回春季年会  2018.3 

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  • 面不斉フェロセンを有するキラルトリアゾリデン Pd 錯体触|rn|媒の合成と不斉鈴木宮浦クロスカップリング反応への利用

    山崎 達郎, 星野 舜, 原口 亮介, 福澤 信一

    日本化学会第98回春季年会  2018.3 

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  • 面不斉フェロセンを有するキラルトリアゾリデン Pd 錯体触 媒の合成と不斉鈴木宮浦クロスカップリング反応への利用

    日本化学会第98回春季年会  2018 

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  • キラル銀および銅触媒を用いたアゾメチンイリドとアルケニルイソオキサゾールとの不斉1,3-双極子環化付加反応

    加藤 萩真, 浅地 早紀, 原口 亮介, 福澤 信一

    74回有機合成化学協会関東支部シンポジウム  2017.11 

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  • 環状ビニルスルホンとアゾメチンイリドとの立体および化学選択的な 1,3-双極子環化付加反応

    原田 真慧, 原口 亮介, 福澤 信一

    第47回複素環化学討論会  2017.10 

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  • 環状ビニルスルホンとアゾメチンイリドとの立体および化学選択的な1,3-双極子環化付加反応

    原田 真慧, 原口 亮介, 福澤 信一

    第7回化学フェスタ  2017.10 

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  • キラルトリアゾリデンパラジウム PEPPSI 錯体の 合成法、特性および不斉鈴木・宮浦クロスカップリン グへの利用

    星野 舜, 原口 亮介, 福澤 信一

    第64回有機金属化学討論会  2017.9 

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  • Silver-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides with benzo[b]thiophene 1,1-dioxides International conference

    Masato Harada, Shin-ichi Fukuzawa

    18th Tetrahedron Symposium  2017.7 

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  • Construction of acyclic all-carbon quaternary stereocenters by gamma-selective formylation of allylzinc bromides

    Ryosuke Haraguchi, Akinori Kusakabe, Nakaba Mizutani, Shin-ichi Fukuzawa

    18th Tetrahedron Symposium  2017.7 

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  • Preparation of Ferrocene-Based Planar Chiral Mesoionic Carbenes and Application in Asymmetric Suzuki-Miyaura Cross-Coupling Reactions

    Shun Hoshino, Ryosuke Haraguchi, Shin-ichi Fukuzawa

    EUCHEMS OMC 2017  2017.7 

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  • チオホルメートを用いた有機亜鉛試薬の新規ホルミル化

    原口亮介, 棚沢翔吾, 日下部瑛規, 福澤信一

    第111回有機合成シンポジウム  2017.6 

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  • 針限結合を鍵活性化に用いる嵩高いルイス酸触媒の創製

    原口亮介, 星野舜, 酒井志徳, 福澤信一

    第111回有機合成シンポジウム  2017.6 

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  • 銀 / ThioClickFerrophos錯体触媒を用いたピロリンエステルとエノンとの不斉1,4-共役付加反応とピロリジジン誘導体の合成

    原田真慧, 小泉昭紘, 原口亮介, 福澤信一

    第73回有機合成化学協会関東支部シンポジウム  2017.5 

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  • キラル銀および銅錯体触媒を用いたアゾメチンイリドとチオナフテンスルホンとの不斉環化付加反応

    原田真慧, 原口亮介, 福澤信一

    日本化学会第97春季年会  2017.3 

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  • Palladium-CatalyzedFormylationofArylzincReagentswithS-PhenylThipformate

    HARAGUCHI Ryosuke・TANAZAWA Sho-go・FUKUZAWA Shin-ichi

    日本化学会第97春季年会  2017.3 

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  • ルテニウム触媒を用いた内部アルキンと第 2 級ジアリールシラ ンの C-H 結合活性化反応を伴う分子間環化反応

    大塚 信彦, 所 雄一郎, 福澤信一

    日本化学会第97春季年会  2017.3 

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  • キラル異常 NHC 配位子の合成及び不斉鈴木・宮浦クロスカッ プリング反応への利用

    原口亮介, 星野 舜, 福澤信一

    日本化学会第97春季年会  2017.3 

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  • Ag/ThioClickFerrophos 錯体触媒を用いたピロリン エステルおよびシアノピロリンとエノンとの不斉 1,4- 共役付加反応

    小泉 昭紘, 鈴木 健 介, 原口 亮介, 福澤 信一

    第63回有機金属化学討論会  2016.9 

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  • キラル金属錯体触媒をもちいたオキサゾリンおよ びチアゾリンエステルからのキラルα,α-二置換アミ ノ酸誘導体の立体多様性合成

    松田 結貴子, 小泉 昭紘, 原口 亮介, 福澤 信一

    第63回有機金属化学討論会  2016.9 

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  • IGAND CONTROLLED DIASTEREOSELECTIVE ASYMMETRIC CONJUGATE ADDITION of 4-OXAZOLINEAND 4-THIAZOLINE ESTERS to NITROALKENES

    Shin-ichi Fukuzawa, Akihiro Koizumi, Yukiko Matsuda

    27th European Colloquium of Heterocyclic Chemistry  2016.7 

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  • 末端ヒドロキシ基を利用したN-ヘテロオルトフェニレンの立体構 制御と構 変換

    日下 部瑛規, 大塚信彦, 所雄一郎, 福澤信一

    第 71 回有機合成化学協会関東支部シンポジウム  2016.5 

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  • キラル 11 族錯体触媒を用いたオキサゾリンエステルおよびチアゾリンエステルとニトロアルケンとの不斉 Michael付加反応

    松田結貴子, 小泉昭紘, 所雄一郎, 福澤信一

    第 71 回有機合成化学協会関東支部シンポジウム  2016.5 

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  • アルキノキシ基を有するフェロセンと内部アルキンとの不斉環化反応

    原田真慧, 杉田健悟, 三井崇, 所雄一郎, 南安規, 檜山爲次郎, 福澤信一

    第 71 回有機合成化学協会関東支部シンポジウム  2016.5 

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  • Copper catalyzed Regioselective C-H Amination of Ferrocenes with Bidentate Directing Group

    Tokoro Yuichiro, Hoshino Shun, Fukuzawa, Shin-ichi

    日本化学会第96春季年会  2016.3 

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  • キラル銅・銀錯体触媒を用いたオキサゾリンおよびチアゾリンエステルとニトロアルケンへの不斉 共役付加反応

    小泉 昭紘, 松田 結貴子, 所 雄一郎, 福澤 信一

    日本化学会第96春季年会  2016.3 

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  • アルキニルフェロセニルエーテルとイソシアナートとのパラジ ウム触媒環化反応

    杉田健悟, 所 雄一郎, 福澤信 一, 南 安規, 檜山爲次郎

    日本化学会第96春季年会  2016.3 

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  • g/ThioClickFerrophos 錯体触媒を用いたピロリン エステルおよびシアノピロリンとエノンとの不斉 1,4- 共役付加反応

    第63回有機金属化学討論会  2016 

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  • Enantio- and diastereoselective conjugate addition of 1-pyrroline 5-carboxylate esters to|rn|nitroalkenes catalyzed by silver and copper complexes with chiral ferrocenyl ligands.

    Kimura Midori, Fukuzawa Shin-ichi

    PACHIFICHEM 2015  2015.12 

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  • パラジウム触媒によるアルキニルフェロセニルエーテルと内部アルキンとの環化付加反応

    杉田健吾, 三井崇, 所雄一郎, 南安規, 檜山為次郎, 福澤信一

    第62回有機金属化学討論会  2015.9 

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  • キラル銀および銅錯体触媒を用いたピロリンエステルのニトロアルケンへの不斉 1,4-共役付加反応

    小泉 昭紘, 木村 緑, 新井 友梨, 松田 結貴子, 所 雄一郎, 福澤 信一

    第62回有機金属化学討論会  2015.9 

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  • Pyrroline 5-Carboxylate Esters to Nitoralkenes Catalyzed by Chiral Silver and Copper Complexes

    Koizumi Akihiro, Kimura Midori, Tokoro Yuichiro, Fukuzawa Shinichi

    OMCOS18  2015.7 

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  • キラル銀及び銅錯体触媒を用いるピロリンエステルのニトロアルケンへの不斉マイケル付加反応

    小泉昭紘, 木村 緑, 所雄一郎, 福澤信一

    第69回有機合成化学協会関東支部シンポジウム  2015.5 

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  • ロジウム触媒によるC-H 結合切断を伴うフェニレンビスアセ|rn|トアミドと内部アルキンのクロスカップリング反応を利用した共役系|rn|高分子の合成

    所雄一郎, 佐藤滉, 福澤信一

    第 95 日本化学会春季年会  2015.3 

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  • キラル銀触媒を用いたピロリンエステルとニトロアルケンとの|rn|1,4-共役付加反応

    小泉昭紘, 木村緑, 新井友梨, 所|rn|雄一郎, 福澤信一

    第 95 日本化学会春季年会  2015.3 

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  • アルキニルフェロセニルエーテルのパラジウム触媒によるC-H|rn|結合活性化を経る内部アルキンとのアニュレーション反応

    三井崇, 所雄一郎, 檜山爲次郎, 福澤信一

    第 95 日本化学会春季年会  2015.3 

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  • ルテニウム触媒によるSi-H 結合とC-H 結合の切断を伴うナフ|rn|チルシランとアルキンの分子間環化反応

    杉田健悟, 所雄一郎, 福澤信一

    第 95 日本化学会春季年会  2015.3 

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  • ジインとビフェニル誘導体の環化反応を利用した非平面構造を|rn|有する多環芳香族炭化水素の合成とその光学特性

    大石杏奈, 所雄一郎, 福澤信一

    第 95 日本化学会春季年会  2015.3 

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  • キラルtzNHC 遷移金属錯体の合成と不斉水素移動反応への応

    登坂拓也, 三井崇, 所雄一郎, 福澤信一

    第 95 日本化学会春季年会  2015.3 

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  • ジインとビフェニル誘導体の環化反応を利用した非平面構造を 有する多環芳香族炭化水素の合成とその光学特性

    第 95 日本化学会春季年会  2015 

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  • ルテニウム触媒によるSi-H 結合とC-H 結合の切断を伴うナフ チルシランとアルキンの分子間環化反応

    第 95 日本化学会春季年会  2015 

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  • アルキニルフェロセニルエーテルのパラジウム触媒によるC-H 結合活性化を経る内部アルキンとのアニュレーション反応

    第 95 日本化学会春季年会  2015 

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  • キラル銀触媒を用いたピロリンエステルとニトロアルケンとの 1,4-共役付加反応

    第 95 日本化学会春季年会  2015 

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  • ロジウム触媒によるC-H 結合切断を伴うフェニレンビスアセ トアミドと内部アルキンのクロスカップリング反応を利用した共役系 高分子の合成

    第 95 日本化学会春季年会  2015 

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  • Enantio- and diastereoselective conjugate addition of 1-pyrroline 5-carboxylate esters to nitroalkenes catalyzed by silver and copper complexes with chiral ferrocenyl ligands.

    2015 

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  • Synthesis of 7-Azabicyclo[2.1.1]heptane-1-Carboxylate via Silver/ThioClickFerrophos-Catalyzed Asymmetric 1,3-Dipolar Cycloaddition of Dihydropyrrole Ester with N-substituted Maleimide

    Atsuo Tada, Midori Kimura, Shin-ichi Fukuzawa

    Vietnam Malaysia International Chemical Congress (VMICC) 2014  2014.11 

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  • ジインとビフェニル誘導体の環化反応を利用した非平面構造を有する多環芳香族炭化水素の合成

    大石杏奈, 所雄一郎, 福澤信一

    第69回有機合成化学協会関東支部シンポジウム  2014.11 

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  • Silver Catalyzed Asymmetric 1,3-Dipolar Cycloaddition of Dihydropyrroles with Activated Alkenes Leading to Synthesis of Bridged Amino Acids

    Shin-ichi Fukuzawa, Atsuo Tada

    5th EuChems Chemsitry Congress  2014.9 

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  • 銀触媒を用いたジヒドロ-2H-ピロール-2-カルボ キシレートおよび 4-オキサゾールカルボキシレートと 活性アルケンとの不斉 1,3-双極子環化付加反応

    夛田 淳生, 所 雄一郎, 福澤 信一

    第61回有機金属討論会  2014.9 

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  • 1,4-ジアダマンチル-1,2,3-トリアゾール-5-イリデ ン配位子の合成とカップリング反応への応用

    三井 崇, 杉原 真人, 所 雄一郎, 福澤 信 一

    第61回有機金属討論会  2014.9 

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  • Silver/ThioClickFerrophos catalyzed enantioselective 1,4-conjugate addition of glycine imino ester to aryl- and alkylidene phosphonates

    Mirori Kimura, Shin-ichi Fukuzawa

    15th Tetrahedron Symposium  2014.6 

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  • Silver catalyzed asymmetric 1,3-dipolar cycloaddition of dihydro-2H-pyrrole-2-carboxylates or 4- oxazolecatboxylates with activated alkenes

    Atsuo Tada, Sayo Watanabe, Shin-ichi Fukuzawa

    15th Tetrahedron Symposium  2014.6 

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  • 銀/ThioClickFerrophos錯体触媒を用いたグリシンイミノエステルとアリーリデンホスホン酸とのエナンチオ選択的な1,4-共役付加反応

    木村緑, 福澤信一

    第68回有機合成化学協会関東支部シンポジウム  2014.6 

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  • 銀錯体触媒を用いたジヒドロピロールエステルの不斉1,3-双極子環化付加反応

    夛田淳生, 渡部紗世, 所雄一郎, 福澤信一

    第68回有機合成化学協会関東支部シンポジウム  2014.5 

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  • 銀錯体触媒を用いたジヒドロピロールエステルの不斉1,3-双極子環化付加反応

    夛田淳生, 所雄一郎

    日本化学会第94春季年会  2014.3 

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  • 1,4−ジアダマンチル1,2,3−トリアゾール−5−イリデン配位子の合成とカップリング反応への応用

    三井崇, 杉原真人, 所雄一郎

    日本化学会第94春季年会  2014.3 

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  • ビフェニル誘導体とアルキンの環化反応を利用した多環芳香族炭化水素の合成

    所雄一郎, 大石安奈

    日本化学会第94春季年会  2014.3 

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  • Palladium/ClickFerrophos Catalyzed Asymmetric Domino Allylstannlation-Heck Reaction of ortho-Formyltriflate

    Atsuo Tada, Yuichiro Tokoro

    International Symposium on Organic Reaction-11  2013.11 

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  • キラル11族金属錯体触媒を用いた環状イミンと電子不足アルケンとの1,3-双極子環化付加反応

    渡辺紗世, 夛田淳生, 所雄一郎

    第66回有機合成化学協会関東支部シンポジウム  2013.11 

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  • AgOAc/ThioClickFerrophos-Catalyzed Base Free Asymmetric Cycloaddition and Conjugate Addition with Imino Esters

    Sayo Watanabe, Takashi Konno, Kenichi Ogata

    17th Organometallic Chemistry Directed Toward Organic Synthesis  2013.7 

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  • Nickel-Catalyzed Ring-Opening Hydroalkynlation of Vinylcyclopropane using Trisisopropylsilylacetylene

    Ayumi Toh, Kenichi Ogata

    17th Organometallic Chemistry Directed Toward Organic Synthesis  2013.7 

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  • Silver/ThioClickFerrophos Catalyzed Enantioselective Conjugate Addition and Cycloaddition of Glycine Imino Ester to Electron Deficient Alkenes

    Takashi Konno, Kazumi Imae

    14th Tetrahedron Symposium  2013.6 

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  • Pd/ClickFerrophos錯体触媒を用いた不斉ドミノアリルスタニル化/Heck反応

    夛田淳生, 緒方賢一

    第65回有機合成化学協会関東支部シンポジウム  2013.5 

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  • tzNHC-PEPPSI型パラジウム触媒の水中檜山カップリングへの応用

    三井崇, 緒方賢一

    第65回有機合成化学協会関東支部シンポジウム  2013.5 

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  • 二官能性触媒―酢酸銀/ThioClickFerrophos錯体を用いるアゾメチンイリドと電子不足アルケンとの不斉1,3‐双極子環化付加反応

    渡部紗世, 徳光千尋, 紺野貴史, 緒方賢一, 福澤信一

    日本化学会第93春季年会  2013.3 

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  • NHC銅錯体を用いるベンゾチアゾールの直接的チオール化反応

    古谷翔一, 猪俣宏, 緒方賢一, 福澤信一

    日本化学会第93春季年会  2013.3 

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  • (2-エチニルピリジン―塩化第一銅)を触媒として用いたアジドとアルキンの1,3―双極子環化付加反応

    廣木英勝, 緒方賢一, 福澤信一

    日本化学会第93春季年会  2013.3 

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  • ニッケル錯体触媒によるトリイソプロピルシリルアセチレンを用いたビニルシクロプロパンの開環を伴うヒドロアルキニル化反応

    藤亜由美, 緒方賢一, 福澤信一

    日本化学会第93春季年会  2013.3 

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  • 銀(I)/ThioClickFerrophos錯体触媒を用いるグリシンイミノエステルとα,β-不飽和エステルとの不斉共役付加反応

    紺野貴史, 緒方賢一, 福澤信一

    第64回有機合成化学協会関東シンポジウム  2012.12 

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  • Asymmetric Conjugate Addition of Glycine Imine to Nitroalkenes catalyzed byAg/ThioClickFerrophos Complex

    Shin-ichi Fukuzawa

    Cambodian Malaysian Chemical Conference  2012.10 

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  • Silver ThioClickFerrophos-Catalyzed Enantioselective conjugate Addition and Cycloaddition ofGlycine Schiff Base with Nitroalkenes

    Takashi Konno, Kazumi Imae|rn|Kenichi Ogata|rn|Shin-ichi Fukuzawa

    25th International Conference on Organometallic Chemistry  2012.9 

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  • ビニルセレノンとアゾメチンイリドとの 1,3-双極子環化付加反応を経るピロール合成

    渡部紗世, 緒方賢一, 福澤信一

    第63回有機合成化学協会関東シンポジウム  2012.5 

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  • 光学活性アミノフェロセンのalpha位置換反応の立体化学の再検証

    高橋樹生, 福澤信一, 緒方賢一

    第63回有機合成化学協会関東支部シンポジウム  2012.5 

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  • ニッケル錯体触媒を用いたエノンとメチレンシクロプロパンの|rn|還元的カップリング反応

    島田大輔, 緒方賢一

    日本化学会第92春季年会  2012.3 

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  • ThioClickFerrophos/銀錯体触媒を用いるイミノエステルとニト|rn|ロアルケンとの不斉Michael 付加反応

    今榮麗仁, 緒方賢一

    日本化学会第92春季年会  2012.3 

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  • ニッケル錯体触媒下におけるメチレンシクロプロパンを利用し|rn|た還元的カップリング反応

    緒方賢一, 島田大輔

    日本化学会第92春季年会  2012.3 

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  • クリックトリアゾール銅錯体を用いたハロゲン化アリールのト|rn|リフルオロメチル化反応

    廣木英勝, 緒方賢一

    日本化学会第92春季年会  2012.3 

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  • 1,2,3-トリアゾールカルベン銅錯体を用いるアゾール類と二酸化|rn|炭素との反応

    猪俣 宏, 緒方賢一, 侯 召民

    日本化学会第92春季年会  2012.3 

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  • 新型ClickFerrophos-ロジウム錯体を用いるalpha,beta-不飽和|rn|リン酸エステルの不斉水素化反応

    紺野貴史, 緒方賢一

    日本化学会第92春季年会  2012.3 

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  • 1,2,3‐トリアゾールNHC‐パラジウムアリル錯体の合成とク|rn|ロスカップリング反応への応用

    猪俣さゆり, 寺島貴大, 緒方賢一

    日本化学会第92春季年会  2012.3 

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  • 1,2,3‐トリアゾールNHC‐パラジウムアリル錯体の合成とク ロスカップリング反応への応用

    日本化学会第92春季年会  2012 

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  • 新型ClickFerrophos-ロジウム錯体を用いるalpha,beta-不飽和 リン酸エステルの不斉水素化反応

    日本化学会第92春季年会  2012 

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  • 1,2,3-トリアゾールカルベン銅錯体を用いるアゾール類と二酸化 炭素との反応

    日本化学会第92春季年会  2012 

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  • クリックトリアゾール銅錯体を用いたハロゲン化アリールのト リフルオロメチル化反応

    日本化学会第92春季年会  2012 

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  • ニッケル錯体触媒下におけるメチレンシクロプロパンを利用し た還元的カップリング反応

    日本化学会第92春季年会  2012 

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  • ThioClickFerrophos/銀錯体触媒を用いるイミノエステルとニト ロアルケンとの不斉Michael 付加反応

    日本化学会第92春季年会  2012 

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  • ニッケル錯体触媒を用いたエノンとメチレンシクロプロパンの 還元的カップリング反応

    日本化学会第92春季年会  2012 

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  • トリアゾールカルベン銅錯体を用いたヘテロ芳香環のカルボキシル化

    猪俣 宏, 緒方賢一, 侯 召民

    第62回有機合成化学協会関東支部シンポジウム  2011.11 

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  • Palladium(II) 1,2,3-triazole-5-ylidene Complexes As Efficient Catalyst for alpha-Arylation of Ketones

    Terashima Takahiro

    XIX European Conference of Organometallic Chemistry  2011.7 

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  • Synthesis of Palladium 1,2,3-Triazol-5-ylidene Complexes and Their Catalysis in Coupling Reactions with Aryl Halides

    Terashima Takahiro

    XIX European Conference of Organometallic Chemistry  2011.7 

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  • 異常1,2,3-トリアゾールNHC-パラジウム錯体の合成と園頭ー萩原カップリング反応

    廣木英勝, 緒方賢一, 福澤信一

    第61回有機合成化学協会関東支部シンポジウム  2011.5 

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  • ニッケル錯体触媒を用いたアルデヒドとメチレンシクロプロパンとの還元的カップリング

    島田大輔, 緒方賢一, 福澤信一

    第61回有機合成化学協会関東支部シンポジウム  2011.5 

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  • 新型ClickFerrophosの合成と不飽和リン酸エステルの不斉水素化反応

    紺野貴史, 緒方賢一, 福澤信一

    第61回有機合成化学協会関東支部シンポジウム  2011.5 

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  • ClickFerrophos/銀錯体触媒を用いるイミノエステルの不斉α-アミノ化反応およびMannich反応

    今榮 麗仁, 緒方 賢一, 福澤 信一

    日本化学会第91春季年会  2011.3 

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  • ClickFerrophos/パラジウム錯体触媒を用いるBuchwald-Hartwigカップリング反応

    芳賀 正剛, 緒方 賢一, 福澤 信一

    日本化学会第91春季年会  2011.3 

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  • ニッケル錯体触媒によるメチレンシクロプロパンあるいはノルボルネンを用いたアリールアルデヒド、シランとの3成分カップリング反応

    緒方 賢一, 厚海 有香, 福澤 信一

    日本化学会第91春季年会  2011.3 

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  • 異常トリアゾールNHC-パラジウムアリル錯体の合成とその触媒作用

    寺島 貴大, 中村 達人, 緒方 賢一, 福澤 信一

    日本化学会第91春季年会  2011.3 

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  • ビス異常トリアゾールNHC−パラジウム錯体の合成と溝呂木−Heck反応

    猪俣 さゆり, 中村 達人, 緒方 賢一, 福澤 信一

    日本化学会第91春季年会  2011.3 

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  • 異常トリアゾールNHC-銅錯体の合成とアジド-アルキン環化付加反応

    中村 達人, 寺島 貴大, 緒方 賢一, 福澤 信一

    日本化学会第91春季年会  2011.3 

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  • Highly chemoselective nickel-catalyzed three-component cross-trimerization of three distinct alkynes

    K. Ogata, Y. Atsuumi, S. Fukuzawa

    PACIFICHEM2010  2010.12 

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  • Synthesis of palladium complex bearing abnormal NHC ligand and application to cross coupling reaction

    T. Nakamura, K. Ogata, S. Fukuzawa

    PACIFICHEM2010  2010.12 

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  • Preparation of new ClickFerrophos ligands and their application to asymmetric synthesis

    K. Imae, K. Shimizu, K. Ogata, S. Fukuzawa

    PACIFICHEM2010  2010.12 

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  • Palladium/ClickFerrophos Complex Catalyzed Suzuki-Miyaura Coupling Reaction of Aryl Chloride

    Masatake Haga, Kenichi Ogata, Shin-Ichi Fukuzawa

    24th ICOMC2010  2010.7 

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  • Nickel-catalyzed Ring-opening Three-component Coupling between Methylenecyclopropane, Arylaldehyde and Silane

    24th ICOMC2010  2010.7 

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  • 銀/ ThioClickFerrophos錯体を用いる,アゾメチンイリドとα,β不飽和エステルとの高エナンチオ選択的1、3双極子環化付加反応

    清水 健太, 大浦 一郎, 緒方 賢一

    日本化学会第90春季年会  2010.3 

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  • 新規アブノーマルNHC-パラジウム錯体の合成と鈴木-宮浦クロスカップリング反応への応用

    中村 達人, 緒方 賢一, 福澤 信一

    日本化学会第90春季年会  2010.3 

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  • Pd/ClickFerrophos錯体を用いる鈴木‐宮浦クロスカップリング反応

    芳賀 正剛, 緒方 賢一

    日本化学会第90春季年会  2010.3 

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  • ニッケル錯体触媒を用いた2分子の異なるアルキンとノルボルネンとの3成分反応

    緒方 賢一, 菅澤 淳, 厚海 有香

    日本化学会第90春季年会  2010.3 

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  • ニッケル錯体触媒を用いた2分子の末端シリルアセチレンとノルボルネン類との3成分反応

    厚海 有香, 菅沢 淳, 緒方 賢一

    日本化学会第90春季年会  2010.3 

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  • 酢酸銀/ThioClickFerrophos錯体を用いた、アゾメチンイリドとα、β不飽和ケトンとの高エナンチオ選択的1、3双極子環化付加反応

    大浦 一郎, 清水 健太, 緒方 賢一

    日本化学会第90春季年会  2010.3 

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  • "銀/ ThioClickFerrophos錯体を用いる,アゾメチンイリドとα,β不飽和エステルとの高エナンチオ選択的1、3双極子環化付加反応"

    日本化学会第90春季年会  2010 

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  • クリックピロリジン構造を持つP,Nー配位子の合成と触媒反応

    今榮 麗仁, 緒方 賢一

    第58回有機合成化学協会関東シンポジウム  2009.11 

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  • ニッケル触媒を用いるアルキンの化学,位置および立体選択的交差三量化反応

    緒方 賢一, 菅沢 淳

    第56回有機金属化学討論会  2009.9 

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  • ニッケル触媒を用いるシリルアルキン,内部アルキン,ノルボルネンの位置および立体選択的三成分交差反応

    菅沢 淳, 緒方 賢一

    第56回有機金属化学討論会  2009.9 

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  • Nickel-catalyzed Highly Chemo, Regio, and Stereoselective Cross-Trimerization of Alkynes Leading to 1,3-Diene-5-ynes

    菅沢 淳, 緒方賢一

    第56回有機金属化学討論会  2009.9 

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  • Fine-tuning of ClickFerrophos Ligands in Asymmetric Hydrogenation of Alkenes and Ketones

    Ichiro Oura, Keiji Oki, Kenichi Ogata

    15th IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis  2009.7 

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  • Nickel-Catalyzed Highly Regio and Stereoselective Cross-Trimerization between Triisopropylsilylacetylene and Internal Alkynes Leading to 1,3-diene-5-ynes

    K. Ogata, J. Sugasawa, H. Mutayama

    15th IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis  2009.7 

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  • Fine-Tuning of ClickFerrophos Ligand in Asymmetric Hydrogenation of Alkenes and Ketones

    Ichiro Oura, Hiroshi Oki, Kenichi Ogata

    15th IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis  2009.7 

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  • ニッケル触媒を用いたトリイソプロピルシリルアセチレンと内部アセチレンとの交差三量化反応

    菅沢 淳, 緒方賢一, 村山宏幸, 岩田智史

    57回有機合成化学協会関東シンポジウム  2009.5 

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  • 新規キラル配位子ーThioClickFerrophos-を用いる不斉アリル置換反応

    中村達人, 大浦一郎, 緒方賢一

    57回有機合成化学協会関東シンポジウム  2009.5 

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  • 金属ClickFerrophos錯体を用いるα,βー不飽和ケトンに対する1.3-双極子環化付加反応

    大浦一郎, 大木啓司, 清水健太, 緒方賢一

    有機合成化学協会関東シンポジウム  2009.5 

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  • Nickel-catalyzed Highly Regio-, and Stereoselective Cross-Trimerization between Triisopropylsilylacetylene and Internal Alkynes Leading to 1,3-Diene-5-ynes

    Kenichi Ogata, Jun Sugasawa, Hiroyuki Murayama

    15th IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis  2009.3 

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  • Nickel-Catalyzed Highly Regiio- and Stereoselective Three-Component Cross-Reaction between Triisopropylsilylacetylene, Internal Alkyne, and Norborne Derivatives

    菅沢 淳, 緒方賢一

    第56回有機金属化学討論会  2009.3 

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  • ニッケル錯体触媒を用いたトリイソプロピルシリルアセチレンと非対称内部アセチレンとの交差3量化反応

    緒方賢一

    第89日本化学会春季年会  2009.3 

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  • ニッケル触媒を用いたトリイソプロピルシリルアセチレンと対象内部アセチレンとの交差3量化反応

    日本化学会春季年会

    村山宏幸,菅沢 淳,緒方賢一  2009.3 

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  • 銅触媒を用いたアゾールC-H結合への直接的チオール化

    厚海有香, 清水瑛治, 芳賀正剛, 緒方賢一

    第89日本化学会春季年会  2009.3 

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  • 銅/ClickFerrophos錯体触媒を用いた不斉還元的アルドール反応

    加藤 実, 大木啓司, 緒方賢一

    第89日本化学会春季年会  2009.3 

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  • 新規ClickFerrophos遷移金属錯体を用いる高選択的不斉水素化

    大木啓司, 加藤 実, 大浦一郎, 緒方賢一

    第89日本化学会春季年会  2009.3 

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  • "クリックピロリジン構造を持つP,Nー配位子の合成と触媒反応"

    第58回有機合成化学協会関東シンポジウム  2009 

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  • ClickFerrophos-銅錯体を用いる不斉1,3-双極子環化付加反応

    大木啓司, 福澤信一

    第88日本化学会春季年会,日本化学会  2008.3 

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  • ClickFerrophos=ロジウム錯体を用いるエナミドの不斉水素化反応

    大浦一郎, 菅沢 淳, 大木啓司, 福澤信一

    日本化学会第88春季年会,日本化学会  2008.3 

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  • クリックケミストリーを用いたキラルフェロセニルホスフィン配位子の合成と不斉反応への応用

    保坂光輝, 福澤信一

    54回有機合成化学協会関東支部シンポジウム,有機合成化学協会関東支部  2007.12 

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  • アミン,アルデヒド,プロピオル酸の三成分連結反応を用いたキノリン合成

    岩井正寛, 菊地哲, 福澤信一

    54回有機合成化学協会関東支部シンポジウム,有機合成化学協会関東支部  2007.12 

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  • 銅触媒を二重触媒として用いるベンジルアセテートからトリアゾールのワンポットクリック合成

    清水瑛治, 菊地哲, 福澤信一

    54回有機金属化学討論会,近畿化学協会  2007.10 

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  • ルイス酸触媒を用いた三成分連結反応によるキノリン及びジヒドロピリジンの合成

    菊地哲, 岩井正寛, 村山宏幸, 福澤信一

    54回有機金属化学討論会,近畿化学協会  2007.10 

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  • Prepation of New Chiral Ferrocenyl Phosphine and Amine Ligands and Their Application to Asymmetric Synthesis

    S. Fukuzawa

    17th International Symposium on Fine Chemistry and Polymers  2007.10 

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  • Three-component Coupling of Amine, Aldehyde, Ethyl Propiolate Catalyzed by Lewis Acid

    Satoshi Kikuchi, Masahiro Iwai, Hiroyuki Murayama, Shin-ichi Fukuzawa

    14th International Symposium on Organometallic Chemistry directed towards Organic Synthesis/IUPAC  2007.8 

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  • Preparation of New Chiral Triazoleferrocenyl Ligands using Click Chemistry

    Hiroshi Oki, Satoshi Kikuchi, Shin-ichi Fukuzawa

    14th International Symposium on Organometallic Chemistry directed towards Organic Synthesis/IUPAC  2007.8 

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  • スカンジウムトリフラートを用いるジヒドロピリジン誘導体の合成

    村山宏幸, 菊地哲, 岩井正寛, 福澤信一

    24回希土類討論会,日本希土類学会  2007.5 

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  • 銅触媒を用いるトリアゾールのワンポットクリック合成

    清水瑛治, 菊地哲, 福澤信一

    53回有機合成化学協会関東支部シンポジウム,有機合成化学協会  2007.5 

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  • 新規キラルフェロセニルトリアゾール配位子(クッリクフェロホス)の合成及び不斉合成への応用

    保坂光輝, 大木啓司, 福沢信一

    日本化学会第87春季年会,日本化学会  2007.3 

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  • オルト-TMS-封鎖フェロセンのリチオ化による新規光学活性フェロセニルホスフィン配位子の合成

    福沢信一, 山本真久

    日本化学会第87春季年会,日本化学会  2007.3 

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  • インジウムトリフラートを用いたキノリン誘導体の合成(2):反応機構とその応用

    菊地 哲, 岩井正寛, 福澤信一

    日本化学会第87春季年会,日本化学会  2007.3 

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  • インジウムトリフラートを用いたキノリン誘導体の合成(1)

    菊地 哲, 岩井正寛, 福澤信一

    日本化学会第87春季年会,日本化学会  2007.3 

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  • サマリウム(Ⅱ)トリフラートを用いたオルト置換面性不斉フェロセニルアルデヒドのピナコールカップリング

    福澤信一, 矢原祐介

    第52回有機合成化学協会関東支部シンポジウム,有機合成化学協会  2006.12 

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  • リン酸基を有する光学活性2級アミンの合成と有機触媒としての応用

    神山 章, 菊地 哲, 福沢信一

    第52回有機合成化学協会関東支部シンポジウム,有機合成化学協会  2006.12 

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  • 新規光学活性フェロセニルホスフィン配位子の合成と不斉反応への応用

    山本真久, 保坂光輝, 菊地 哲, 福澤信一

    第53回有機金属化学討論会,近畿化学協会  2006.9 

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  • Preparation of New Chiral Ferrocenyl Diamines and Their Related Compounds and Their Application to Asymmetric Synthesis

    Mitsuteru Hosaka, Masahisa Yamamoto, Satoshi Kikuchi, Shin-ichi Fukuzawa

    XXIIth Inthernational Symposium on Organometallic Chemsitry/IUPAC  2006.7 

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  • サマリウム金属種を用いたイミンの不斉還元とその応用

    岩井正寛, 菊地 哲, 福沢信一

    第23回希土類討論会,日本希土類学会  2006.5 

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  • Pd触媒を用いたジスルフィドおよびジセレニドとハロゲン化アリールとのカップリング反応

    谷原大亮, 菊地 哲, 福沢信一

    日本化学会第86春季年会,日本化学会  2006.3 

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  • オキサゾリン及びピリジン骨格を有する新規フェノール誘導体の合成と応用

    高嶋宗光, 菊地 哲, 福沢信一

    日本化学会第86春季年会,日本化学会  2006.3 

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  • サマリウム金属種を用いたイミンの不斉還元

    岩井正寛, 菊地 哲, 福沢信一

    日本化学会第86春季年会,日本化学会  2006.3 

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  • 光学活性ビスフェロセニルジオール/イッテルビウム錯体を触媒とする不斉Diels-Alder反応

    矢原祐介, 保坂光輝, 菊地 哲, 福沢信一

    日本化学会第86春季年会,日本化学会  2006.3 

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  • ビス(オキサゾリン)ピリジン希土類トリフラート錯体触媒を用いる高エナンチオ選択的Michael付加反応

    菊地 哲, 岩井正寛, 佐藤広秋, 福沢信一

    日本化学会第86春季年会,日本化学会  2006.3 

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  • 光学活性ビスフェロセニルジアミン配位子の合成と不斉水素転移反応への応用

    阿部麻美, 鈴木貴志, 福沢信一

    日本化学会第86春季年会,日本化学会  2006.3 

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  • A facile synthesis of a New Chiral Ferrocene based on Binaphtyl Chiral Auxiliary

    Masahisa Yamamoto, Shin-ichi Fukuzawa

    PACIFIHEM 2005/American Chemical Society, Chemical Society of Japan etc  2005.12 

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  • Preparation of Chiral ortho-Substituted Diferrocenyl 1,2-Diol and Its Application to Asymmetric Cycloadditions

    Akira Kamiyama, Shin-ichi Fukuzawa

    PACIFICHEM 2005/American Chemical Society, Chemical society of Japan  2005.12 

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  • Preparation of New Chiral Bisferrocenyl Oxazoline by Pinacol Coupling of Chiral Formylferrocenes and Its Application to Asymmetric Synthesis

    Masumi Hara, Shin-ichi Fukuzawa

    Recent Advances in Catalysis/University of Rennes 1  2005.9 

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  • Preparation of Chiral 1,4-Ferrocenyl Diazide and Diamide and Their Derivatives

    Takashi Suzuki, Shin-ichi Fukuzawa

    Recent Advances in catalysis 2005/Univerisity of Rennes 1  2005.9 

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  • 希土類/ピボックス錯体を触媒とする不斉アザマイケル反応

    佐藤広秋, 菊地 哲, 福沢信一

    第52回有機金属化学討論会,近畿化学協会  2005.9 

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  • 二価のサマリウム錯体を用いるオルト置換キラルホルミルフェロセンのピナコールカップリング

    神山 章, 原 真純, 福沢信一

    第22回希土類討論会,日本希土類学会  2005.5 

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  • 二価のサマリウムトリフラートを用いる面性不斉ホルミルフェロセンのピナコールカップリング反応

    福澤信一, 原 真純, 神山 章

    第85日本化学会春季年会,日本化学会  2005.3 

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  • 光学活性1,4-フェロセニルジアジドおよびジアミンの合成

    福澤信一, 鈴木貴志

    第85日本化学会春季年会,日本化学会  2005.3 

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  • 新規光学活性トリカルコゲナフェロセン誘導体の合成

    福澤信一, 和智大介, 土田昌平

    第85日本化学会春季年会,日本化学会  2005.3 

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  • Chiral Rare Earth Complex Catalyzed Asymmetric Cycloaddition Reactions

    Shin-ichi Fukuzawa

    Rare Earth '04 in Nara JAPAN  2004.11 

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  • 超臨界二酸化炭素中ハイブリッド系中における不斉D-els-Alder反応

    佐藤広秋, 矢原祐介, 福澤信一

    第51回有機金属化学討論会,近畿化学協会  2004.10 

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  • Regioselective and Stereospecific Aminolysis and Hydrolysis of Chiral 1,4-Ferrocenyl Diacetate: Preparation of New Chiral Ferrocenyl Ligands

    Shin-ichi Fukuzawa, Takashi Suzuki, Daisuke Wachi

    XXIst International Conference on Organometallic Chemistry  2004.7 

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  • キラルなサレン希土類錯体を用いる不斉アルキル亜鉛付加反応

    佐藤広秋, 長田全弘, 福澤信一

    第21回希土類討論会,希土類学会 希土類学会  2004.5 

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  • 銅トリフラート/box触媒を用いる超臨界に酸化炭素中における不斉ディールズーアルダー反応

    江角真一, 樋浦竹彦, 福澤信一

    日本化学会第84春季年会,日本化学会 日本化学会  2004.3 

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  • 1,2-置換フェロセンの合成と変換反応:利き腕を持つキラルフェロセン

    伊藤 智, 福澤信一

    日本化学会第84春季年会,日本化学会 日本化学会  2004.3 

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  • Chiral Rare Earth Complex Asymmetric Diels-Alder Reaction in Supercritical Carbon Dioxide

    International Symposium on Organic Synthesis/National Sun Yatsen University  2003.12 

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  • Chiral Rare Earth/Bisimine Complex Catalyzed Enantioselective Carbonyl Enene Reaction and 1,3-Dipolar Reaction

    Narihito Nakano, Yoshitaka Kmuro, Shin-ichi Fukuzawa

    50th Symposium on Organometallic Chemsitry/Kinki Chemical Society  2003.9 

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  • Preparation and Transformation of Chiral 1,2-Disubstituted Ferrocenes; The Chiral Ferrocene with a Stronger Arm

    Satoshi Itoh, Daisuke Wachi, Tadamune Otsubo, Shin-ichi Fukuzawa

    50th Symposium on Organometallic Chemsitry/Kinki Chemical Society  2003.9 

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  • Preparation and Transformation of Chiral 1,2-disubstituted Ferrocenes: A Chiral Ferrocene with a Better Arm

    Shin-ichi Fukuzawa, Satoshi Itoh

    Dalton Discussions 6: Organometallic Chemistry and Catalysis/Royal Society of Chemistry  2003.9 

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  • ランタノイド金属ーイソプロパノール系を用いるカルボニル化合物の還元反応

    樋浦竹彦, 斉藤隆英, 福沢信一

    日本化学会第83春季年会,日本化学会  2003.3 

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  • サレンー希土類錯体を用いる不斉環化付加反応

    中野成人, 小室嘉崇, 福沢信一

    日本化学会第83春季年会,日本化学会  2003.3 

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  • キラルな希土類錯体触媒を用いる超臨界に酸化炭素中における不斉Diels-Alder反応:反応の選択性に及ぼす二酸化炭素の密度効果

    江角真一, 福沢信一

    日本化学会第83春季年会,日本化学会  2003.3 

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  • キラルな希土類錯体触媒を用いる超臨界二酸化炭素中における希不斉ヘテロDiels-Alder反応

    江角真一, 目時健, 福沢信一

    第42回有機合成化学協会関東支部シンポジウム、A15(長岡)  2001.11 

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  • ヨウ化サマリウム(Ⅱ)によるキラルケトンまたはアルデヒドとキラルα、βー不飽和エステルとのカップリング反応によるとの速度論的光学分割

    三浦学, 福沢信一

    第48有機金属化学討論会、PB 211(横浜)  2001.9 

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  • 光学活性1、2 置換フェロセニルホスフィンの合成と不斉合成反応への応用

    藤本邦昭, 福沢信一

    第48有機金属化学討論会、PB 138(横浜)  2001.9 

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  • 超臨界二酸化炭素中における希土類ルイス酸錯体触媒を用いる不斉Diels-Alder反応

    目時健, 江角真一, 福沢信一

    第80日本化学会秋季年会、2G1 07(千葉)  2001.9 

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  • Rare Earth(II) Lewis Acid Catalysed Asymmetric Diels-Alder Reaction in Supercritical Carbon Dioxide

    Ken Metoki, Shin-ichi Fukuzawa

    11th Symposium on Organometallic Chemistry directed toward Organic Synthesis, P208, Taipei  2001.7 

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  • Scandium(III) Triflate/1,2-Ferrocendiol Complex Catalyzed Asymmetric Diels-Alder Reaction

    Yoshitaka Komuro, Kuniaki Fujimoto, Shin-ichi Fukuzawa

    11th Symposium on Organometallic Chemistry directed toward Organic Synthesis, P208, Taipei  2001.7 

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  • Synthesis of Chiral 1,2-Ferrocenyldiphosphines and Their Application to Asymmetric Synthesis

    Kuniaki Fujimoto, Masaya Egawa, Shin-ichi Fukuzawa

    11th Symposium on Organometallic Chemistry directed toward Organic Synthesis, P208, Taipei  2001.7 

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  • Samarium(II) Iodide Mediated Kinetic resolution of Chiral Ketones and Aldehydes by the Coupling Reaction with Chiral Acrylic Acid Esters

    Manabu Miura, Atsushi Satoh, Shin-ichi Fukuzawa

    11th Symposium on Organometallic Chemistry directed toward Organic Synthesis, P208, Taipei  2001.7 

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  • 希土類金属系触媒によるブタジエンとスチレンの立体特異的重合

    会田昭二郎, 侯召民, 若槻康雄, 斉藤隆英, 福沢信一

    第79日本化学会春季年会、1D1 35(神戸)  2001.3 

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  • ヨウ化サマリウム(Ⅱ)を用いるキラルなα、βー不飽和エステルとのカップリング反応によるキラルケトンまたはアルデヒドとの速度論的光学分割

    三浦学, 佐藤敦, 松沢啓史, 福沢信一

    第79日本化学会春季年会、1H1 06(神戸)  2001.3 

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  • 超臨界二酸化炭素中における希土類ルイス酸錯体触媒を用いるホモキラルなジエノフィルとジエンとの不斉Diels-Alder反応

    小室嘉崇, 目時健, 松沢啓史, 福沢信一

    第79日本化学会春季年会、1G5 30(神戸)  2001.3 

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  • キラルな1、2 フェロセンジオールー希土類錯体を触媒として用いる不斉Diels-Alder反応

    松沢啓史, 目時健, 福沢信一

    第79日本化学会春季年会、1G5 29(神戸)  2001.3 

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  • pybox-希土類錯体を触媒として用いる不斉Diels-Alder反応

    松沢啓史, 目時健, 福沢信一

    第79日本化学会春季年会、1G5 28(神戸)  2001.3 

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  • 光学活性1、2 フェロセニルホスフィンの合成と不斉合成反応への応用

    藤本邦昭, 江川雅也, 菊池華世子, 高杉友洋, 福沢信一

    第79日本化学会春季年会、3G4 13(神戸)  2001.3 

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  • ヨウ化サマリウム(Ⅱ)を用いるキラルなα、β-不飽和エステルとキラルなケトンまたはアルデヒドとのカップリング反応

    佐藤敦, 三浦学, 福沢信一

    第40回有機合成化学協会関東支部シンポジウム、2A-2、(新潟)  2000.11 

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  • キラルなアミノ及びアシルフェロセンへの有機金属反応剤のジアステレオ選択的付加

    藤本邦昭, 福沢信一

    第47回有機金属化学討論会、PB-139(京都)  2000.10 

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  • 希土類トリフラートーキラル配位子を用いる不斉Diels-Alder反応

    日時健, 渋谷寛政, 小室嘉崇, 松沢啓史, 福沢信一

    第78回有機合成シンポジウム、P-22(京都)  2000.9 

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  • Diastereoselective Reduction snd C-C Bond Formation of Homochiral alpha-Keto Esters/Amides by Smamarium(II) Iodide

    Matsuzawa Hiroshi, Shin-ichi Fukuzawa

    PACIFICHEM 2000, Honolulu, USA  2000.7 

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  • Diastereoselective Reduction snd C-C Bond Formation of Homochiral alpha-Keto Esters by Smamarium(II) Iodide

    Shin-ichi Fukuzawa

    4th International Symposium on Transition Metals in Organic Synthesis, Leeds, UK  2000.7 

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  • Diastereoselective Alkylation and Reduction of Chiral Formyl and Acylferrocenes

    Takeshi A.Sawai, Shin-ichi Fukuzawa

    PS-172/19th IUPAC International Conference on Organometallic Chemistry, Shanghai, China  2000.7 

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  • ヨウ化サマリウム(Ⅱ)を用いるキラルなα-およびβ-ケトエステルの不斉還元反応とアリル化反応

    吉満真一, 松沢啓史, 福沢真一

    第78回日本化学会春季年会、3F2-25(船橋)  2000.3 

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  • キラルなアミノアシルフェロセンの還元反応

    澤井剛, 土屋大輔, 福沢信一

    第78回日本化学会春季年会、3F2 26、(船橋)  2000.3 

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  • 1、1’-ジアセチル及びジホルミルフェロセンとSm12との反応

    藤本邦昭, 土屋大輔, 福沢信一

    第78回日本化学会春季年会、3F2 27、(船橋)  2000.3 

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  • 1、1’-および1、2-二置換キラルフェロセン化合物の合成とこれらを用いる不斉有機合成反応

    土屋大輔, 澤井剛司, 福沢信一

    第38回有機合成化学協会関東支部シンポジウム(新潟)  1999.12 

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  • 二価のサマリウム錯体を用いる不斉有機合成反応

    福沢信一

    希土類講演会(東京)  1999.11 

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  • キラルなホルミルフェロセンの合成と反応

    笹本華絵, 藤本邦明, 福沢信一

    第77回日本化学会秋季年会(札幌)  1999.9 

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  • Synthesis of optical activity 1,2-hetero disubstitued ferrocene compounds and their application to asymmetrics synthesis

    Shin-ichi Fukuzawa, Daisuke Tsuchiya, Kohki Hirano

    10th IUPAC Symposium on Organometallic Chemistry Directed Toward Organic Synthesis, Versailles, France  1999.7 

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