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Catalytic Asymmetric Reactions Means of Attractive Interactions

Research Project

Project/Area Number 07454163
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionKyoto University

Principal Investigator

HAYASHI Tamio  Kyoto University, Department of Chemistry Professor, 大学院・理学研究科, 教授 (00093295)

Project Period (FY) 1995 – 1996
Project Status Completed (Fiscal Year 1996)
Budget Amount *help
¥7,700,000 (Direct Cost: ¥7,700,000)
Fiscal Year 1996: ¥2,500,000 (Direct Cost: ¥2,500,000)
Fiscal Year 1995: ¥5,200,000 (Direct Cost: ¥5,200,000)
KeywordsCatalytic Asymmetric Synthesis / Attractive Interactions / Chiral Monophosphines / Chiral Ferrocenylphosphines / Chiral Bisoxazolines / Asymmetric Oxidation / Asymmetric Substitutions / 光学活性単座配位子 / ワッカー型反応 / MOP配位子 / 軸不斉ビナフチル / 光学活性ビスオキサゾリン / boxax配位子 / 不斉ヒドロシリル化
Research Abstract

Asymmetric reactions catalyzed by transition metal complexes containing optically active phosphine ligands have attracted significant interest for their synthetic utility. One of the most exciting and challenging subjects in research on the catalytic asymmetric synthesis is development of the chiral ligand which will fit in with a given reaction efficiently in enantioselectivity as well as in catalytic activity. In designing chiral ligands we have attached importance to introduction of a functional group into the ligand that, where possible, would be expected to interact attractively with a functional group in the substrate. The attractive interactions will enhance the enantioselectivity in catalytic asymmetric reactions by increased steric interactions between the chiral ligand and a prochiral substrate. We have developed new chiral ligands bearing some functional groups on the backbone : 1) 2- (Diphenylphosphino) -1,1'-binaphthyls (MOPs) which have carboxyl, hydroxy, alkoxy, and amino groups on the 2'-position. 2) Ferrocenyl-and ruthenocenylbisphosphines containing amino and hydroxy groups on the metallocene side chain. 3) Several kinds of functional groups were introduced into 3-and 3'-positions of 2,2'-bis [4- (alkyl) oxazol-2-yl] -1,1'-binaphthyls (boxax). These functionalized chiral ligands have been used for palladium-catalyzed asymmetric reactions including allylic substitutions and Wacker-type cyclization.

Report

(3 results)
  • 1996 Annual Research Report   Final Research Report Summary
  • 1995 Annual Research Report
  • Research Products

    (28 results)

All Other

All Publications (28 results)

  • [Publications] 魚住泰広: "Homochiral 2,2'-Bis (oxazolyl) -1,1'-binaphthyls as Chiral Ligands for Copper (I)-Catalyzed Asymmetric Cyclopropanation" Tetrahedron Asymmetry. 7. 1603-1606 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] 林 民生: "Erythro-Selective Aldol-Type Reaction of N-Sulfonylaldimines with Methyl Isocyanoacetate Catalyzed by Gold (I)" Tetrahedron Lett.37. 4969-4972 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] 林 民生: "Catalytic Asymmetric Synthesis of Optically Active Olefins by Palladium-Catalysed Asymmetric Reduction of Racemic Allylic Esters with Formic Acid" Chem. Commun.1767-1768 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] 林 民生: "Stereochemistry in Palladium-Catalyzed Cyclization Forming a Vinyldihydrofuran via π-Allylpalladium Intermediate" J. Org. Chem.62. 204-207 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] 林 民生: "Regio-and Enantioselective Allylic Alkylation Catalyzed by Chiral Monophosphine-Palladium Complexes" Chem. Commun.(in press).

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] 魚住泰広: "Catalytic Asymmetric Wacker-Type Cyclization" J. Am. Chem. Soc.(in press).

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] 林 民生: "Ferrocenes" VCH Verlagsgesellshaft, 1-540 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Yasuhiro Uozumi: "Homochiral 2,2'-Bis (oxazolyl) -1,1'-binaphthyls as Chiral Ligands for Copper (I) -Catalyzed Asymmetric Cyclopropanation" Tetrahedron Asymmetry. 7. 1603-1606 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Tamio Hayashi: "Erythro-Selective Aldol-Type Reaction of N-Sulfonylaldimines with Methyl Isocyanoacetate Catalyzed by Gold (I)" Tetrahedron Lett.37. 4969-4972 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Tamio Hayashi: "Catalytic Asymmetric Synthesis of Optically Active Olefins by Palladium-Catalysed Asymmetric Reduction of Racemic Allylic Esters with Formic Acid" Chem.Commun.1767-1768 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Tamio Hayashi: "Stereochemistry in Palladium-Catalyzed Cyclization Forming a Vinyldihydrofuran via pi-Allylpalladium Intermediate" J.Org.Chem.62. 204-207 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Tamio Hayashi: "Regio- and Enantioselective Allylic Alkylation Catalyzed by Chiral Monophosphine-Palladium Complexes" Chem.Commun.(in press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Yasuhiro Uozumi: "Catalytic Asymmetric Wacker-Type Cyclization" J.Am.Chem.Soc.(in press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Tamio Hayashi: Ferrocenes. VCH Verlagsgesellshaft, 1-540 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] 魚住泰広: "Homochial 2'2′Bis(oxazolyl)-1,1′-binaphthyls as Chiral Ligands Copper(I)-Catalyzed Asymmetric Cyclopropanation" Tetrahedron Asymmetry. 7. 1603-1606 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] 林民生: "Erythro-Selective Aldol-Type Reaction of N-Sulfonylaldimines with Methyl Isocyanoacetate Catalyzed by Gold(I)" Tetrahedron Lett.37. 4969-4972 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] 林民生: "Catalytic Asymmetric Synthesis Optically Active Olefins by Palladium-Catalysed Asymmetric Reduction of Racemic Allylic Esters with Formic Acid" Chem.Commun.1767-1768 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] 林民生: "Stereochemistry in Palladium-Catalyzed Cyclization Forming a Vinyldihydrofuran via π-Allypalladium Intermediate" J.Org.Chem.62. 204-207 (1997)

    • Related Report
      1996 Annual Research Report
  • [Publications] 林民生: "Regio-and Enantioselective Allylic Alkylation Catalyzed by Chiral Monophosphine-Palladium Complexes" Chem.Commun.(in press).

    • Related Report
      1996 Annual Research Report
  • [Publications] 魚住泰広: "Catalytic Asymmetric Wacker-Type Cyclization" J.Am.Chem.Soc.(in press).

    • Related Report
      1996 Annual Research Report
  • [Publications] 林民生: "Ferrocenes" VCH Verlagsgesellshaft, 1-540 (1995)

    • Related Report
      1996 Annual Research Report
  • [Publications] 魚住泰広: "Asymmetric Hydrosilylation of 1-Alkenes Catalyzed by Palladium-MOP" Bull. Chem. Soc. Jpn.68. 713-722 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] 北山健司: "Palladium-Catalysed Asymmetric Hydrosilylation of Styrenes with a New Chiral Monodentate Phosphine Ligand" J. Chem. Soc., Chem. Commun.1533-1534 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] 林 民生: "Catalytic Asymmetric Synthesis of Axially Chiral Biaryls by Palladium-Catalyzed Enantioposition-Selective Cross-Coupling" J. Am. Chem. Soc.117. 9101-9102 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] 大野 晃: "Preparation of Chiral Ferrocenylphosphines Containing New Alkyl Substituents on the Ferrocenylmethyl Position" Tetrahedron Asymmetry. 6. 2495-2502 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] 林 民生: "Catalytic Asymmetric Hydrosilylation of Ketones with New Chiral Ferrocenylphosphine-Imine Ligands" Tetrahedron Asymmetry. 6. 2503-2506 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] 神川 卓: "Enantioposition-Selective Alkynylation of Biaryl Ditriflates by Palladium-Catalyzed Asymmetric Cross-Coupling" Tetrahedron Lett.(in press).

    • Related Report
      1995 Annual Research Report
  • [Publications] 林 民生: "Ferrocenes" VCH Verlagsgesellshaft, 1-540 (1995)

    • Related Report
      1995 Annual Research Report

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Published: 1995-04-01   Modified: 2016-04-21  

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