Hg(OAc)2 mediated highly regio- and/or diastereoselective allylic tert-acetylation of olefins

Abstract

Isolation of reaction intermediates facilitated a mechanistic investigation of the known Hg(OAc)₂ mediated aromatisation reaction of carvone. We propose a different mechanism for this reaction than the previously proposed mechanism. The reaction method was further exploited for the highly regio- and/or diastereoselective allylic oxidation of geminally disubstituted olefins to allylic tert-acetates and applied in the total synthesis of andirolactone.