Highly enantioselective construction of tricyclic derivatives by the desymmetrization of cyclohexadienones

Abstract

The asymmetric synthesis of tricyclic compounds by the desymmetrization of cyclohexadienones is presented. The reaction tolerated a large variety of substituents at different positions of the cyclohexadienone, and heterocyclic rings of different sizes were accessible. Density functional theory calculations showed that the reaction proceeds through an asynchronous [4+2] cycloaddition.

Keywords: asymmetric synthesis; desymmetrization; dienamines; intramolecular Diels-Alder reactions; organocatalysis.