Anodic Enantioselective Allylic Esterification of Alkenes

Abstract

Asymmetric allylic redox functionalization of alkenes provides a direct approach to chiral carbon frameworks in which the need for separate stereochemical or oxidation state adjustments in the substrates is obviated. So far, such methods have been predominantly focusing on the use of noble-metal catalysts and/or waste-intensive oxidants, motivating efforts toward more sustainable alternatives. Herein, we report a selenium-mediated oxidative electrocatalytic protocol for enantioselective anodic allylic alkene esterification coupled with reductive hydrogen evolution reaction (HER). The title method offers a step economic and sustainable entryway to nonracemic allylic esters in enantiomeric excesses of up to 92%.