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.
Nicola Di Iorio, Paolo Righi, Andrea Mazzanti, Michele Mancinelli, Alessia Ciogli, Giorgio Bencivenni (2014). Remote Control of Axial Chirality: Aminocatalytic Desymmetrization of N-Arylmaleimides via Vinylogous Michael Addition. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 136, 10250-10253 [10.1021/ja505610k].
Remote Control of Axial Chirality: Aminocatalytic Desymmetrization of N-Arylmaleimides via Vinylogous Michael Addition
DI IORIO, NICOLA;RIGHI, PAOLO;MAZZANTI, ANDREA;MANCINELLI, MICHELE;BENCIVENNI, GIORGIO
2014
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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
