One‐Pot Stereoselective Synthesis of 2,3,4‐Unprotected β‐N‐Glycopyranosides from Glycals and Amines

Abstract

AbstractA one‐pot synthesis of 2,3,4‐unprotected β‐N‐glycopyranosides from glycals and amines with exclusive β‐stereoselectivity under room temperature conditions is reported. This method was achieved via palladium‐catalyzed Tsuji‐Trost amination followed by dihydroxylation directly, tolerating anilines, heterocyclic aromatic amines, and N,O‐dimethylhydroxylamine, especially the reaction of primary amines and glycals has not been reported before. Furthermore, the protocol was applied to modify clinical drugs (prazosin, imiquimod) and construct the analogue of the natural product amphimedoside A.