General Strategy for Stereoselective Synthesis of β-<i>N</i>-Glycosyl Sulfonamides via Palladium-Catalyzed Glycosylation

Abstract

A highly efficient and mild glycosylation reaction between 3,4- O-carbonate glycal and N-tosyl functionalized aliphatic and aromatic amines via palladium-catalyzed decarboxylative allylation is disclosed. A wide range of highly functionalized 2,3-unsaturated β- N-glycosides are furnished in good to excellent yields and complete regioselectivity and stereoselectivity. In addition, applications of the glycosyl sulfonamides as the precursor to assemble functional derivatives have also been explored, including glycosylation, dihydroxylation, and nucleophilic addition to the N-glycosides.