Permanganate oxidation of α,β-unsaturated carbonyls to vicinal tricarbonyls

Abstract

Vicinal tricarbonyl compounds (VTCs) are useful synthetic intermediates. Most synthetic methods of VTCs require toxic oxidants under cryogenic conditions or noble transition metal catalysis. In this study, we report an expedient synthesis of VTCs from cheap and easily available α,β-unsaturated carbonyls through permanganate oxidation under phase transfer condition. The key to this process is the presence of acetic acid additive that enhances the oxidation ability of permanganate.