Stereospecific Palladium-Catalyzed Direct Glycosylation of Oximes: Access to N–O-Linked Glycosides

Abstract

A highly efficient, palladium-catalyzed glycosylation between 3,4- O -carbonate glycals and acid-labile oximes is disclosed. This approach features broad substrate scope, high functional group tolerance, and easy scalability, delivering glycosyl oximes in excellent yields with exclusive β-selectivity and retention of Z / E geometries. The power of this method is demonstrated by a set of site-selective transformations of glycosylation products and late-stage glycodiversification of bioactive molecules. Overall, our strategy provides an efficient toolkit for facile access to valuable N–O-linked glycosides.

Topics & Concepts