| Project/Area Number |
05453181
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| Research Category |
Grant-in-Aid for General 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, ISIR,Professor, 産業科学研究所, 教授 (50114575)
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| Co-Investigator(Kenkyū-buntansha) |
ICHIHARA Junko Osaka University, ISIR,Research Assistant, 産業科学研究所, 教務職員 (60110772)
KANAI Motomu Osaka University, ISIR,Research Associate, 産業科学研究所, 助手 (20243264)
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| Project Period (FY) |
1993 – 1994
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| Project Status |
Completed (Fiscal Year 1994)
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| Budget Amount *help |
¥7,500,000 (Direct Cost: ¥7,500,000)
Fiscal Year 1994: ¥1,500,000 (Direct Cost: ¥1,500,000)
Fiscal Year 1993: ¥6,000,000 (Direct Cost: ¥6,000,000)
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| Keywords | Asymmetric synthesis / Chiral catalyst / Organolithiums / Chiral diether / Anino ether / beta-Lactam / Imines / Conjugate addition / 機能性キラル分子 / 不斉合成 / 不斉触媒 / キラルエーテル / アミン / 触媒反応 |
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| Research Abstract |
Asymmetric synthesis of chiral molucules of excellent function in a large scale is one of the most important challenges in recent synthetic chemistry. For this purpose, design of a novel catalytic cycle and chiral catalyst is essential. We have found that catalytic chiral diether and amino ether promte the reaction of organolithiums in nonpolar medium. The activation is caused by deaggregation of organolithiums by these donor catalysts. This concept was extended to quite promising reactions as shown below.
1. Catalytic asymmetric synthesis of beta-lactam of high ee by the reaction of lithium ester enolate with imine in the presence of 5 mol% chiral amino ether catalyst.
2. Catalytic asymmetric synthesis of anines of more than 90% ee by the reaction of organolithium with imines.
3. Catalytic asymmetric conjugate reaction of organolithiums to alpha, beta-unsaturated esters was performed in high ee in the presence of chiral diether catalyst.
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