1991 Fiscal Year Final Research Report Summary
The Molecular Design of Chiral Crown Ethers as Efficient Asymmetric Catalysts.
| Project/Area Number |
02557085
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| Research Category |
Grant-in-Aid for Developmental Scientific Research (B)
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| Allocation Type | Single-year Grants |
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| Research Field |
Chemical pharmacy
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| Research Institution | University of Tokyo |
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Principal Investigator |
KOGA Kenji Faculty of Pharmaceutical Sciences, University of Tokyo, Professor., 薬学部, 教授 (10012600)
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| Co-Investigator(Kenkyū-buntansha) |
AOKI Shin Faculty of Pharmaceutical Sciences, University of Tokyo, Assistant., 薬学部, 助手 (00222472)
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| Project Period (FY) |
1990 – 1991
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| Keywords | Chiral Crown Ethers / Chiral Complexes / Catalytic Asymmetric Reactions / Enantioselective Reactions / Michael Reactions |
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| 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).
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