Palladium-catalyzed glycal imidate rearrangement: formation of alpha- and beta-N-glycosyl trichloroacetamides.Org Lett. 2007 Oct 11; 9(21):4231-4.OL
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.