A Convenient Multigram Synthesis of Highly Enantioenriched Methyl 3-Silylglycidates

Abstract

A multigram scale synthesis of the four stereoisomers of methyl 3-silylglycidates (epoxysilanes) with high enantiopurity is described. Key reactions include a Sharpless asymmetric epoxidation (SAE) of a trans-vinylsilane and an enzymatic resolution of a racemic cis-epoxysilane to establish the desired configurations. Few chromatographic separations (5 columns out of 13 steps) are required for purification, establishing a convenient reaction sequence for both the trans- and cis-isomers.