Electrochemically driven stereoselective approach tosyn-1,2-diol derivatives from vinylarenes and DMF

Abstract

We have developed an electrochemically driven strategy for the stereoselective synthesis of protectedsyn-1,2-diols from vinylarenes withN,N-dimethylformamide (DMF). The newly developed system obviates the need for transition metal catalysts or external oxidizing agents, thus providing an operationally simple and efficient route to an array of protectedsyn-1,2-diols in a single step. This reaction proceedsviaan electrooxidation of olefin, followed by a nucleophilic attack of DMF. Subsequent oxidation and nucleophilic capture of the generated carbocation with a trifluoroacetate ion is proposed, which gives rise predominantly to asyn-diastereoselectivity upon the second nucleophilic attack of DMF.