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1996 Fiscal Year Final Research Report Summary

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
KeywordsCatalytic Asymmetric Synthesis / Attractive Interactions / Chiral Monophosphines / Chiral Ferrocenylphosphines / Chiral Bisoxazolines / Asymmetric Oxidation / Asymmetric Substitutions
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.

  • Research Products

    (14 results)

All Other

All Publications (14 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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [Publications] 林 民生: "Ferrocenes" VCH Verlagsgesellshaft, 1-540 (1995)

    • Description
      「研究成果報告書概要(和文)」より
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [Publications] Tamio Hayashi: Ferrocenes. VCH Verlagsgesellshaft, 1-540 (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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