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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 (1997-1998)  Niigata College of Pharmacy, Faculty of Pharmaceutical Sciences, Research Associate, 薬学部, 助手 (20267652)

武内 征司 (1996)  新潟薬科大学, 薬学部, 助教授 (00131011)

Co-Investigator(Kenkyū-buntansha) 中村 豊  新潟薬科大学, 薬学部, 助手 (20267652)
Project Period (FY) 1996 – 1998
Project Status Completed (Fiscal Year 1998)
Budget Amount *help
¥2,300,000 (Direct Cost: ¥2,300,000)
Fiscal Year 1998: ¥300,000 (Direct Cost: ¥300,000)
Fiscal Year 1997: ¥200,000 (Direct Cost: ¥200,000)
Fiscal Year 1996: ¥1,800,000 (Direct Cost: ¥1,800,000)
Keywordssamarium enolate / enantioselective protonation / catalytic reaction / ヨウ化サマリウム / C_2-対称キラルジオール
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.

Report

(4 results)
  • 1998 Annual Research Report   Final Research Report Summary
  • 1997 Annual Research Report
  • 1996 Annual Research Report
  • Research Products

    (6 results)

All Other

All Publications (6 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
    • Related Report
      1998 Final Research Report Summary
  • [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
    • Related Report
      1998 Final Research Report Summary
  • [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
    • Related Report
      1998 Final Research Report Summary
  • [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
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Seiji Takeuchi et al: "Catalytic Enantioselective Protonation of a Samarium Enolate with Fluorous Chiral and Achiral Proton Sources in Fluorous Biphasic Systems" Tetrahedron Letters. 39(47). 8691-8694 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] 中村豊: "Catalytic Enantioselective Protonation of Samarium Enolates by A C_2-Symmetric Chiral Diol" Tetrahedron Letters. 37・16. 2805-2808 (1996)

    • Related Report
      1996 Annual Research Report

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Published: 1996-04-01   Modified: 2016-04-21  

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