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1998 Fiscal Year Final Research Report Summary

Studies on catalytic enantioselective protonation

Research Project

Project/Area Number 08640699
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionNiigata College of Pharmacy

Principal Investigator

NAKAMURA Yutaka  Niigata College of Pharmacy, Faculty of Pharmaceutical Sciences, Research Associate -> 新潟薬科大学, 薬学部, 助手 (20267652)

Project Period (FY) 1996 – 1998
Keywordssamarium enolate / enantioselective protonation / catalytic reaction
Research Abstract

(1) Enantioselectivities near maximum values were obtained in the catalytic enantioselective protonation of samarium enolate by a rapid addition of a fluorous achiral alcohol (Rfh_33C-OH) to the reaction mixture : for a nonfluorous chiral diol (DHPEX) in Rfh_3C-OH/THF solid-liquid biphase system and for a fluorous chiral alcohol in THF/FC-72 liquid-liquid biphase system.
(2) High enantioselectivity (up to 94% ee) has been achieved in the enantioselective protonation of samarium enolates generated by SmI_2-mediated reductive elimination of alpha-hetero-substituted ketones using C_2-symmetric chiral diol as a proton source.

Research Products

(4 results)

All Other

All Publications

  • [Publications] Seiji Takeuchi: "Catalytic Enantioselective Protonation of a Samarium Enolate with Fluorous Chiral and Achiral Proton Sources in Fluorous Biphasic Systems" Tetrahedron Letters. 39. 8691-8694 (1998)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Yutaka Nakamura: "Enantioselective Protonation of Samarium Enolates Derived from α-heterosubstituted Ketones and Lactones by SmI_2-Mediated Reduction" Tetrahedron. 55. 4595-4620 (1999)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Seiji Takeuchi: "Catalytic Enantioselective Protonation of a Samarium Enolate with Fluorous Chiral and Achiral Proton Sources in Fluorous Biphasic Systems" Tetrahedron Lett. 39(47). 8691-8694 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Yutaka Nakamura: "Enantioselective Protonation of Samarium Enolates Derived from alpha-heterosubstituted Ketones and Lactones by SmI_2-Mediated Reduction" Tetrahedron. 55(15). 4595-4620 (1999)

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

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Published: 1999-12-07  

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