N-Heterocyclic Carbene-Catalyzed Desymmetrization of Siladials To Access Silicon-Stereogenic Organosilanes.

Abstract

An N-heterocyclic carbene (NHC)-catalyzed enantioselective monoesterification of silicon-centered dialdehydes with alcohols or phenols is accomplished, providing optically active organosilanes bearing a stereogenic center at the silicon atom. This desymmetrization protocol is suitable for scale-up synthesis and late-stage modifications of complex molecules, and the products can be further transformed to other enantiopure functionalized silanes.