1993 Fiscal Year Final Research Report Summary
Asymmetric Synthesis Using Chiral Lewis Base
| Project/Area Number |
04557097
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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 | Osaka University |
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Principal Investigator |
TOMIOKA Kiyoshi Osaka University The Institute of Scientific and Industrial Research Professor, 産業科学研究所, 教授 (50114575)
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| Co-Investigator(Kenkyū-buntansha) |
INOUE Isao Tanabe Seiyaku Ltd.Researcher, 製薬技術センター, 研究員
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| Project Period (FY) |
1992 – 1993
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| Keywords | Asymmetric synthesis / Chiral catalyst / Organolithium / Amino ether / Chiral ether / beta-Lactam / Amines / Catalytic reaction |
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| Research Abstract |
Chiral Lewis base coordinates to metallic center of metallic reagents and activates the reagent. Consequently, it is highly probable that stereochemical control of the reaction would be achieved by coordination of the chiral Lewis base to metal. However, the use of chiral Lewis base in the reaction is quite rare in the modern synthetic chemistry. This is clearly contrasted to the familiar use of chiral Lewis acid as activator as well as stereoconytoller.
In the present research we focused on design, synthesis, and application of chiral Lewis base into asymmetric synthesis. Moreover, we applied the chiral Lewis base as a chiral catalyst in the reaction which can produce optically active compounds more than the equivalence of the chiral catalyst.
As a result of the studies we developed quite promising reactions as shown below.
1. Asymmetric synthesis of beta-lactam of more than 90% ee by the reaction of lithium ester enolate with imine in the presence of chiral amino ether catalyst.
2. Catalytic asymmetric synthesis of highly optically active beta-lactam using catalytic amount of chiral amino ether.
3. Catalytic asymmetric synthesis of amines of more than 90% ee by the reaction of organolithium with imines.
These promising results may open a new world of synthetic organic chemistry and its application to the industrial production.
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