Novel stereospecific nucleophilic addition reaction to optically active vinyl sulfoxide

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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.