| Project/Area Number |
02640414
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| Research Category |
Grant-in-Aid for General Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Research Field |
有機化学一般
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| Research Institution | Okayama University of Science |
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Principal Investigator |
NOKAMI Junzo Okayama University of Science Department of Applied Chemistry Associate Professor, 工学部, 助教授 (70109742)
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| Project Period (FY) |
1990 – 1991
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| Project Status |
Completed (Fiscal Year 1991)
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| Budget Amount *help |
¥2,200,000 (Direct Cost: ¥2,200,000)
Fiscal Year 1991: ¥400,000 (Direct Cost: ¥400,000)
Fiscal Year 1990: ¥1,800,000 (Direct Cost: ¥1,800,000)
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| Keywords | Optically Active Sulfoxide / Vinyl Sulfoxide / Stereospecific Nucleophilic addition / Asymmetric Induction / Three Contiguous Chiral Carbon Chain / Lithium Enolate / Quarternary Asymmetric Carbon / 3連続不斉炭素 / リチウムエノレ-ト |
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| Research Abstract |
1. Lithium enolates derived from ethyl or tert-butyl alkanoates with lithium diisopropylamide (LDA) and from ethyl 2-alkenoate with lithium N-benzyltrimethylsilyiamide (LSA) reacted with optically active vinyl sulfoxides to give stereospecific nucleophilic addition products possessing two or three contiguous chii'al carbon chain.
2. Useful building block having a quartenary asymmetric carbon which would play an efficient role in organic synthesis was built by employin8 the stereospecific nucleophi I ic addition of acetic esterenolate to beta beta-disubstitu ted optica]Iy active vinyl sulfoxide.
3. Brefeldin A was synthesi2ed by using (+)-4-cyanomethylcyclopent-2-en-l-one as a key compound. 4-Hydroxy-2-enoate functionality was built by the reaction of the aidehydeintermediate with (S)-ethyl p-chlorophenyisulfinylacetate.
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