Combined Computational and Experimental Studies on the Asymmetric Michael Addition of α-Aminomaleimides to β-Nitrostyrenes Using an Organocatalyst Derived from Cinchona Alkaloid
Combined Computational and Experimental Studies on the Asymmetric Michael Addition of α-Aminomaleimides to β-Nitrostyrenes Using an Organocatalyst Derived from Cinchona Alkaloid
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DOI：
10.1021/acs.orglett.1c01831
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发表时间：
2021-07-13
期刊：
影响因子：
5.2
通讯作者：
Oriyama, Takeshi
中科院分区：
文献类型：
--
作者：
Sakai, Naoki;Kawashima, Kyohei;Oriyama, Takeshi
在传统的反应中，马来酰亚胺通常被用作亲电剂；然而，它们作为亲核剂的应用仅限于少数几个反应，并且利用α-氨基马来酰亚胺作为不对称Michael供体的反应到目前为止还没有报道。因此，在这项工作中，作为Michael供体的α-氨基马来酰亚胺与β-硝基苯乙烯的不对称Michael加成反应是首次使用从金鸡纳生物碱衍生的有机催化剂进行的。密度泛函理论研究是提高加合物对映体选择性的关键。
Maleimides are often used as electrophiles in conventional reactions; however, their application as nucleophiles is limited to only a few reactions, and reactions utilizing alpha-aminomaleimides as asymmetric Michael donors have not been reported to date. Thus, in this work, asymmetric Michael addition of alpha-aminomaleimides as Michael donors to beta-nitrostyrenes was conducted for the first time using an organocatalyst derived from a Cinchona alkaloid. Density functional theory investigations were crucial to improve the enantioselectivity of the adduct.