Access to Complex C2-Branched Glycoconjugates via Palladium-Catalyzed Aminocarbonylation Reaction of 2-Iodoglycals.

A convenient and straightforward synthesis of 2-amidoglycals through a palladium-catalyzed aminocarbonylation reaction between 2-iodoglycal partners and diverse amines in the presence of a "CO" source has been developed. Several amines such as aliphatics, benzylics, or aromatics are compatible with our reaction conditions as well as sulfonamides. Further deprotection steps have been successfully applied, leading to glycoside mimics. This method constitutes a new route to access original glycopeptide- and glycolipid-type analogues possessing a C-C bond at the C2-position.