Glycosamine Derivatives through Metal‐Catalyzed C−N Bond Formation on Protected and Unprotected 2‐Iodoglycals

Abstract

AbstractGlycosamines are important building blocks of natural biopolymers. The development of synthetic routes to such glycoside family is of big interest in terms of biological application. Herein, access to glycosamine derivatives through dual nickel/copper‐catalyzed C−N bond formation via a cross‐coupling reaction is presented. Diverse benzyl‐ and cyclic amide‐containing glycals were successfully synthesized in moderate to excellent yields starting from perbenzylated and protecting group‐free 2‐iodoglycals. 16 examples presenting d‐glucal or d‐galactal configuration and an electron‐rich or electron‐poor amide moiety in position 2 of the carbohydrate are obtained by this methodology. Post‐functionalization by hydrogenolysis conditions of three synthesized compounds allows access to d‐mannosamine and d‐talosamine mimics.