Remote Control of Axial Chirality: Aminocatalytic Desymmetrization of <i>N</i>-Arylmaleimides via Vinylogous Michael Addition

Abstract

Remote control of the axial chirality of N-(2-t-butylphenyl)succinimides was realized via the vinylogous Michael addition of 3-substituted cyclohexenones to N-(2-t-butylphenyl)maleimides. 9-Amino(9-deoxy)epi-quinine promoted the enantioselective desymmetrization, leading to atropisomeric succinimides with two adjacent stereocenters.