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1991 Fiscal Year Final Research Report Summary

The Molecular Design of Chiral Crown Ethers as Efficient Asymmetric Catalysts.

Research Project

Project/Area Number 02557085
Research Category

Grant-in-Aid for Developmental Scientific Research (B)

Allocation TypeSingle-year Grants
Research Field Chemical pharmacy
Research InstitutionUniversity of Tokyo

Principal Investigator

KOGA Kenji  Faculty of Pharmaceutical Sciences, University of Tokyo, Professor., 薬学部, 教授 (10012600)

Co-Investigator(Kenkyū-buntansha) AOKI Shin  Faculty of Pharmaceutical Sciences, University of Tokyo, Assistant., 薬学部, 助手 (00222472)
Project Period (FY) 1990 – 1991
KeywordsChiral Crown Ethers / Chiral Complexes / Catalytic Asymmetric Reactions / Enantioselective Reactions / Michael Reactions
Research Abstract

The design of efficient catalysts for asymmetric reactions has been a recent focus in synthetic organic chemistry.
Crown ethers are anticipated to be efficient catalysts for C-C bond formations, because they have been proved to complex with metal cations and activate counteranions.
The asymmtric Michael, - addition of methyl phenylthioacetate 2 to 2 - cyclohexenone 3 is a good reaction to obtain optically active delta - ketoester derivative (4). The optical purity of C-3 position of 4 was determined by conversion of 4 to 5, the reductive desul-furization with (nBu)_4 SnH in a good yield. We have found that C_2-svmmetric 1 complexed with KOtBu (10mol%) catalyzes the Michael reaction of 2 and induces the relatively high enantioselectivity(71%e. e. S).

  • Research Products

    (4 results)

All Other

All Publications (4 results)

  • [Publications] S.Aoki,S.Sasaki,and K.Koga: "Simple Chiral Crown Ethers Complexed with Potassium test-Butoxide as Efficient Catalyst for Asymmetric Michael Additions" Tetrahedron Letters. 30. 7229-7230 (1989)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] S.Aoki,S.Sasaki,and K.Koga: "Michael Addition Reactions to 2-Cyclopentenone Catalyzed by Chiral Crown-KOtBu Complexes" Heterocycles. 33. (1992)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] S. Aoki, S. Sasaki, and K. Koga: "Simple Chiral Crown Ethers Complexed with Potassium tert - Butoxide as Efficient Catalysts for Asymmetric Michael Additions." Tetrahedron Letters. 30. 7229-7230 (1989)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] S. Aoki, S. Sasaki, and K. Koga: "Asymmetric Michael Addition Reactions of Methyl Phenylthioacetate t+ 2 - cyclopentenone Catalyzed by Chiral Crown - KOtBu Complexes." Heterocycles. 33. (1992)

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

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Published: 1993-03-16  

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