Study on the Synthesis of Optically Active Silacyclopentanes and their Application to Asymmetric Synthesis
Project/Area Number |
05650886
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Research Category |
Grant-in-Aid for General Scientific Research (C)
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Allocation Type | Single-year Grants |
Research Field |
Synthetic chemistry
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Research Institution | Science University of Tokyo |
Principal Investigator |
NAGAO Yukinori Faculty of Science and Technology, Science University of Tokyo Associate Professor, 理工学部, 助教授 (30089370)
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Project Period (FY) |
1993 – 1994
|
Project Status |
Completed (Fiscal Year 1994)
|
Budget Amount *help |
¥1,400,000 (Direct Cost: ¥1,400,000)
Fiscal Year 1994: ¥700,000 (Direct Cost: ¥700,000)
Fiscal Year 1993: ¥700,000 (Direct Cost: ¥700,000)
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Keywords | Silacyclopentane / Silacyclopentene / Optically active / Hydrogenation / Diphenylbutadiene / Silyl enol ether / Racemic mixture / Diastereomer / 光学分割 / アルドール型反応 |
Research Abstract |
Alkoxy derivatives of 2,5-diphenylsilacyclopent-3-ene were prepared by one-pot reaction of (E,E) -diphenyl-1,3-butadiene, dialkoxydichlorosilanes, and magnesium in THF.The obtained silacyclopentenes included trans rich isomer. The reaction with alkyltrichlorosilanes gave only cis isomer. The hydrogenation of these silacyclopentenes gave corresponding silacyclopentanes. Then the alkoxy derivatives of silacyclopentenes were lithiated with LDA.The reaction of the lithio silacyclopentenes with alkyl bromides gave 2-alkyl substituted 1,1-dialkoxy-2,5-diphenylsilacyclopent-3-enes and unreacted trans isomer of silacyclopemtenes. Next, the reaction of 1,1-diethoxy-2,5-diphenylsilacyclopent-3-ene with optically active alcohols (1-menthol and 1-borneol) were investigated and the racemic mixture gave diastereomer. Furthermore, 1,2,5-trimethylsilacyclopentane was prepared by the reaction of grignard reagent of 2,5-dibromohexane with methyldichlorosilane and silyl enol ether was prepared by the reaction of 1-methyl-1-chloro-2,5-diphenylsilacyclopentene with cyclohexanone.
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Report
(3 results)
Research Products
(3 results)