Stereoselective carbon–carbon bond formation <i>via</i> 1,2-asymmetric induction by a β-substituent in the reaction of α-chloro sulfides with organozinc reagents

Abstract

The stereoselectivity of C–C bond formation in the reaction of α-chlorosulfides with a variety of organozinc reagents has been investigated. The study reveals excellent 1,2-asymmetric induction by a β-siloxy substituent and moderate 1,2-induction by the β-methyl substituent. The stereoselectivity is a function of the size of the organozinc reagents.