Tin (IV)-Mediated Stereoselective Synthesis of Epoxides with Concomitant Alkyl Peroxide Formation.

Abstract Epoxy alkyl peroxides are formed stereoselectively by the action of t -butyl hydroperoxide-SnCl 4 upon allylic alcohols containing an amido group, and with reversal of the diastereoselectivity shown by the action of t -butyl hydroperoxide-VO(acac) 2 upon analogous carbocyclic alcohols.