The Journal of Organic Chemistry

Oxazolines. XX. Synthesis of achiral and chiral thiiranes and olefins by reaction of carbonyl compounds with 2-(alkylthio)-2-oxazolines

AI Meyers, ME Ford

Index: Meyers,A.I.; Ford,M.E. Journal of Organic Chemistry, 1976 , vol. 41, p. 1735 - 1742

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Citation Number: 74

Abstract

Metalation of 2-(alkylthio)-2-oxazolines (6-12) followed by addition of a variety of carbonyl compounds leads to thiiranes 17 in 60-70% yield. The process is also useful for the direct synthesis of alkenes and dienes by extrusion of the sulfur from thiiranes. In many cases a high degree of stereoselectivity is observed in the alkene formation. An asymmetric synthesis of chiral thiiranes has also been achieved providing these substances in 19-32 ...