Bulletin of the Chemical Society of Japan p. 2153 - 2158 (1991)
Update date:2022-08-05
Topics:
Satoh, Tsuyoshi
Hayashi, Yasumasa
Yamakawa, Koji
Addition of the carbanion of 1-chloroalkyl p-tolyl sulfoxide to carbonyl compounds gave the adducts, which were heated in refluxing toluene or xylene to give vinyl chlorides in high overall yield.Dehydrochlorination of the vinyl chlorides with excess n-BuLi afforded propargylic alcohols in high yields.Asymmetric synthesis of both enantiomers of the propargylic alcohols was realized using optically active 1-chloroalkyl p-tolyl sulfoxide and aldehyde.
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