Direct, stereoselective thioglycosylation enabled by an organophotoredox radical strategy.

ABSTRACT: While strategies involving a 2e^- transfer pathway have dictated glycosylation development, the direct glycosylation of readily accessible glycosyl donors as radical precursors is particularly appealing because of high radical anomeric selectivity and atom- and step-economy. However, the development of the radical process has been challenging owing to notorious competing reduction, elimination and/or S_N side reactions of commonly used, labile glycosyl donors. Here we introduce an organophotocatalytic strategy through which glycosyl bromides can be efficiently converted into corresponding anomeric radicals by photoredox mediated HAT catalysis without a transition metal or a directing group and achieve highly anomeric selectivity. The power of this platform has been demo

SUBMITTER: Ji P 

PROVIDER: S-EPMC8163235 | biostudies-literature | 2020 Oct

REPOSITORIES: biostudies-literature