1991 Fiscal Year Final Research Report Summary

Novel stereospecific nucleophilic addition reaction to optically active vinyl sulfoxide

Research Project

Project/Area Number	02640414
Research Category	Grant-in-Aid for General Scientific Research (C)
Allocation Type	Single-year Grants
Research Field	有機化学一般
Research Institution	Okayama University of Science
Principal Investigator	NOKAMI Junzo Okayama University of Science Department of Applied Chemistry Associate Professor, 工学部, 助教授 (70109742)
Project Period (FY)	1990 – 1991
Keywords	Optically Active Sulfoxide / Vinyl Sulfoxide / Stereospecific Nucleophilic addition / Asymmetric Induction / Three Contiguous Chiral Carbon Chain / Lithium Enolate / Quarternary Asymmetric Carbon
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.

(4 results)