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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, 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 (4 results)

  • [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: 1999-12-08  

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