A stereoselective organocatalyzed C-glycosylation of indole: implications of acceptor–catalyst–donor interactions†

Abstract

A stereoselective pyridinium hexafluorophosphate-catalyzed C-glycosylation of indole is presented, featuring the plausible formation of a catalyst–acceptor complex and a crucial H-bond between the N–H group of indole and the oxygen atom at the C6 position of the glycosyl donor, which are proposed to collectively facilitate the glycosylation process. This reaction proceeds under mild conditions, enabling the selective synthesis of a wide range of C-indolyl glycosides.