Remote Control of Axial Chirality: Aminocatalytic Desymmetrization of N-Arylmaleimides via Vinylogous Michael Addition
Journal of the American Chemical Society2014Vol. 136(29), pp. 10250–10253
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Nicola Di Iorio, Paolo Righi, Andrea Mazzanti, Michele Mancinelli, Alessia Ciogli, Giorgio Bencivenni
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.
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