Electrochemical enantioselective dihydroxylation reaction of N-alkenyl nucleobases for the construction of chiral acyclic nucleosides

Abstract

A simple and sustainable KI-mediated electrochemical enantioselective dihydroxylation reaction of N-alkenyl nucleobases was developed for the first time in an undivided cell. A series of chiral acyclic nucleosides bearing two adjacent hydroxyl groups and stereogenic carbon centers in the corresponding side chain were obtained in up to 97% yield and 98% ee with only a 0.1 mol% Os catalyst. Moreover, this reaction featuring a high TON (up to 950) and exogenous oxidant-free conditions provides an efficient and environmentally benign synthetic route to chiral acyclic nucleosides.