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1996 Fiscal Year Final Research Report Summary

Typical Metal-Catalyzed Asymmetric Synthesis

Research Project

Project/Area Number 05234105
Research Category

Grant-in-Aid for Scientific Research on Priority Areas

Allocation TypeSingle-year Grants
Research InstitutionNagoya University

Principal Investigator

YAMAMOTO Hisashi  Nagoya University, Graduate School of Engineering, Professor, 工学部, 教授 (10135311)

Co-Investigator(Kenkyū-buntansha) NAKAI Takeshi  Tokyo Institute of Technology, Department of Chemical Technology, Professor, 工学部, 教授 (90016717)
TAMAO Kouhei  Kyoto University, Institute for Chemical Research, Professor, 化学研究所, 教授 (60026218)
SUZUKI Keisuke  Keio University, Department of Chemistry, Professor, 理工学部, 教授 (90162940)
SHIOIRI Takayuki  Nagoya City University, Faculty of Pharmaceutical Sciences, Professor, 薬学部, 教授 (20012627)
OGUNI Nobuki  Yamaguchi University, Faculty of Science, Professor, 理学部, 教授 (60028165)
Project Period (FY) 1993 – 1995
Keywordstypical metal-catalyzed asymmetric synthesis / asymmetric Diels-Alder reaction / asymmetric protonation / asymmetric addition-ring opening reaction / chiral quaternary salt / stereospecific 1,2-rearrangement / asymmetric intramolecular hydrosilation / asymmetric allylation
Research Abstract

Asymmetric synthesis has developed rapidly and extensively, and is now growing into a new way of producing optically active chiral compounds that is more general and efficient than enzymatic reactions in many cases. The aim of project "typical metal-catalyzed asymmetric synthesis, " was executed by many organic chemists diving into six research groups of "development and application of designer Lewis acid (Yamamoto), " "asymmetric reactions of diketene with aldehydes catalyzed by chiral Schiff base-titanium complexes (Oguni), " "asymmetric synthesis utilizing chiral quaternary salt catalysts and chiral auxiliaries from monoterpenes (Shioiri), " "some new ways of organometallicbased stereocontrol (Suzuki), " "asymmetric intramolecular hydrosilation (Tamao), " and "development of catalytic asymmetric reactions (Nakai)" for three years beginning in 1993. This project was not only create various new asymmetric reactions by taking advantage of characteristics of typical elements, but also to apply many enantio- and diastereoselective reactions to the synthesis of the complex multi-chiral compounds including useful natural products. During 1993-1995, many new asymmetric or stereoselective reactions related to Diels-Alder reaction (Yamamoto), protonation (Yamamoto), addition-ring opening reaction of diketenes with aldehydes (Oguni), aldol reaction (Shioiri), addition of silylacetylenes to carbonyl compounds (Shioiri), 1,2-rearrangement of alkynyl groups (Suzuki), metallo-ene reaction (Suzuki), intramolecular hydrosilation (Tamao), addition of aldehydes with diethylzinc (Nakai), and allylation (Nakai) were developed.

  • Research Products

    (16 results)

All Other

All Publications (16 results)

  • [Publications] H.Yamamoto: "First Example of a Highly Enantioselective Catalytic Protonation of Silyl Enol Ethers." J.Am.Chem.Soc.118. 12854-12855 (1996)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] N.Oguni: "Highly Efficient Preparation of Optically Active 5-Hydroxy-3-oxoesters by Enantioselective Reaction of Diketene with Aldehydes Promoted by Novel Chiral Sciff Base-Titanium Alkoxide Complexes." Tetrahedron Asymmetry. 6. 1833-1836 (1995)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] T.Shioiri: "Tetrahenylphosphonium Hydrogendifluoride:A New Catalyst for Silyl-mediated Aldol Reaction and the Addition of Silylacetylenes to Carbonyl Compounds" Synlett. 1033-1034 (1995)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] K.Suzuki: "Total Synthesis of(+/-)-Furaquinocin D." J.Am.Chem.Soc.117. 10757-10758 (1995)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] K.Tamao: "Silyl Anions" Adv.Organomet.Chem.38. 1-58 (1995)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] T.Nakai: "Asymmetric Catalysis by a New Type of Chiral Binaphthol-Titanium Complex" Tetrahedron Lett.36. 1861-1864 (1995)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] H.Yamamoto: "Advances in Catalytic Processes,Volume 1" JAI Press Inc., 194(31) (1995)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] T.Nakai: "Advances in Catalytic Processes,Volume 1" JAI Press Inc., 194(26) (1995)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] H.Yamamoto: "First Example of a Highly Enantioselective Catalytic Protonation of Silyl Enol Ethers." J.Am.Chem.Soc.118. 12854-12855 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] N.Oguni: "Highly Efficient Preparation of Optically Active 5-Hydroxy-3-oxoesters by Enantioselective Reaction of Diketene with Aldehydes Promoted by Novel Chiral Sciff Base-Titanium Alkoxide Complexes." Tetrahedron Asymmetry. 6. 1833-1836 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T.Shioiri: "Tetraphenylphosphonium Hydrogendifluoride : A New Catalyst for Silyl-mediated Aldol Reaction and the Addition of Silylacetylenes to Carbonyl Compounds" Synlett. 1033-1034 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] K.Suzuki: "Total Synthesis of (+/-) Furaquinocin D." J.Am.Chem.Soc.117. 10757-10758 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] K.Tamao: "Silyl Anions" Adv.Organomet.Chem.38. 1-58 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T.Nakai: "Asymmetric Catalysis by a New Type of Chiral Binaphthol-Titanium Complex" Tetrahedron Lett.36. 1861-1864 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] H.Yamamoto: Advances in Catalytic Processes, Volume 1. JAI Press Inc., 29-59 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T.Nakai: Advances in Catalytic Processes, Volume 1. JAI Press Inc., 124-149 (1995)

    • Description
      「研究成果報告書概要(欧文)」より

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Published: 1999-03-09  

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