Palladium(ii)-catalyzed stereoselective synthesis of C-glycosides from glycals with diaryliodonium salts

Abstract

An efficient palladium(ii) mediated C-glycosylation of glycals with diaryliodonium salts is described, providing a new strategy for the synthesis of 2,3-dideoxy C-aryl glycosides with excellent stereoselectivity. The C-glycosylation of a diverse range of glycals, including d-glucal, d-galactal, d-allal, l-rhamnal, l-fucal, l-arabinal, d-maltal, and d-lactal, occurred effectively and the corresponding C-glycosides were obtained in moderate to good yields. This protocol is commended as a significant addition to the field of carbohydrate chemistry due to the rich functional group compatibility, broad range of substrate scope and exceptional α-stereoselectivity.