Diastereoselective Aldol Reactions of Enolates Generated from Vicinally Substituted Trimethylsilylmethyl Cyclopropyl Ketones

Abstract

(Equation presented) Vicinally substituted trimethylsilylmethyl cyclopropyl ketones undergo facile desilylative ring opening with Lewis acids under mild conditions. The enolates, thus generated, undergo aldol addition with aldehydes and ketones. The diastereoselectivity of the reaction with aldehydes depends on the nature of the Lewis acid used. The resulting aldol product is easily converted into a substituted tetrahydrofuran derivative.