Stereoselective Hydrocyanation of Alkenyl Sulfoxides as a Method to Highly Enantiomerically Enriched Compounds with Tertiary and Quaternary Chiral Carbon Atoms

Abstract

Terminal alkynes are easily transformed into enantiomerically enriched compounds containing tertiary and quaternary carbon atoms. Sulfinylation followed by reduction (or alkylation) and hydrocyanation of the resulting vinyl sulfoxides with Et2AlCN provides nitriles bearing the chiral center, which can in turn undergo reaction to form the desired products (see reaction scheme). Tol=4‐tolyl.