Stereoselective synthesis of C-glycosides from glycals and organotrifluoroborate salts

Abstract

Harnessing aryltrifluoroborates’ stability and reactivity, we developed a Pd-catalyzed stereoselective C-glycosylation under ambient conditions, yielding diverse C-aryl glycosides with exclusive α-stereoselectivity and compatibility with hydroxyl, amide, and amine groups. This method enables functionalization to produce unprotected C-pyranosides, 2,3-dideoxy and 2,3-epoxy sugars, and late-stage C-glycosylation of natural products and drugs.