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

We have developed an electrochemically driven strategy for the stereoselective synthesis of protected -1,2-diols from vinylarenes with ,-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 protected -1,2-diols in a single step. This reaction proceeds an 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 a -diastereoselectivity upon the second nucleophilic attack of DMF.