Photocatalytic synthesis of difluorinated glycoamino acids and neoglycopeptides via hydrodifluoroacetamidation of vinyl-C-glycosides

Abstract

A photocatalytic approach for the synthesis of difluorinated glycoamino acids and neoglycopeptides from bromodifluoroacetamides and sugar-derived olefins is presented. This method stands out because of its simplicity, atomic economy, and mild reaction conditions, allowing compatibility with both natural and unnatural amino acids and peptides. Additionally, it demonstrates efficacy across a variety of carbohydrates, including furanoses, pyranoses, pentose, hexoses, and disaccharides, accommodating an extensive range of protecting groups, even in their deprotected forms.