Palladium-Catalyzed Glycal Imidate Rearrangement: Formation of α- and β-<i>N</i>-Glycosyl Trichloroacetamides

Abstract

A novel palladium(II)-catalyzed stereoselective synthesis of alpha- and beta-N-glycosyl trichloroacetamides has been developed. The alpha- and beta-selectivity at the anomeric carbon depends on the nature of the palladium-ligand catalyst. While the cationic palladium(II) promotes the alpha-selectivity, the neutral palladium(II) favors the beta-selectivity.