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

A one-pot synthesis of 2,3,4-unprotected & beta;-N-glycopyranosides from glycals and amines with exclusive & beta;-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.

Automated summary

A 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, achieved via palladium-catalyzed Tsuji-Trost amination followed by dihydroxylation directly, can tolerate anilines, heterocyclic aromatic amines, and N,O-dimethylhydroxylamine. Particularly, the reaction of primary amines and glycals has not been reported before. Furthermore, this protocol has been successfully applied in the modification of clinical drugs (prazosin, imiquimod) and the construction of an analogue of natural product amphimedoside A.