Remote Control of Axial Chirality: Aminocatalytic Desymmetrization of N-Arylmaleimides via Vinylogous Michael Addition
Remote Control of Axial Chirality: Aminocatalytic Desymmetrization of N-Arylmaleimides via Vinylogous Michael Addition
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DOI：
10.1021/ja505610k
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发表时间：
2014-07-23
影响因子：
15
通讯作者：
Bencivenni, Giorgio
中科院分区：
文献类型：
--
作者：
Di Iorio, Nicola;Righi, Paolo;Bencivenni, Giorgio
通过3-取代环己酮与N-(2-叔丁基苯基)马来酰亚胺的乙烯基迈克尔加成反应，实现了N-(2-叔丁基苯基)丁二酰亚胺的轴向手性远程控制。9-氨基(9-脱氧)表奎宁促进了对映体选择性去对称化反应，生成了具有两个相邻立体中心的异构体琥珀酰亚胺。
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.