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.
Remote control of axial chirality: aminocatalytic desymmetrization of N‑arylmaleimides via vinylogous Michael Addition / N., Di Iorio; P., Righi; A., Mazzanti; M., Mancinelli; Ciogli, Alessia; G., Bencivenni. - In: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY. - ISSN 0002-7863. - 136:29(2014), pp. 10250-10253. [10.1021/ja505610k]
Remote control of axial chirality: aminocatalytic desymmetrization of N‑arylmaleimides via vinylogous Michael Addition
CIOGLI, Alessia;
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.| File | Dimensione | Formato | |
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