A Cation-Directed Enantioselective Sulfur-Mediated Michael/Mannich Three-Component Domino Reaction involving Chalcones as Michael Acceptors
A Cation-Directed Enantioselective Sulfur-Mediated Michael/Mannich Three-Component Domino Reaction involving Chalcones as Michael Acceptors
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DOI：
10.1021/acs.orglett.5b01833
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发表时间：
2015-09-04
期刊：
影响因子：
5.2
通讯作者：
Peng, Yungui
中科院分区：
文献类型：
--
作者：
Ding, Ran;Zheng, Bo;Peng, Yungui
发展了一种以查尔酮为Michael受体的不对称硫介导的三组分分子间Michael/Mannich多米诺反应的新方法。该反应由改性奎宁衍生的手性季铵盐催化，可以轻松获得具有三个连续立体中心的复杂含硫化合物，产率高达93%，其中dr为95：5，ee为95%。这些化合物被进一步阐述，得到相当于手性氮杂-森田-贝利斯-希尔曼反应的产物，涉及查尔酮和带有四个手性中心的氮杂环丁烷。
A new approach has been developed for an asymmetric sulfur-mediated three-component intermolecular Michael/Mannich domino reaction using chalcones as Michael acceptors. This reaction is catalyzed by chiral quaternary ammonium salts derived from modified quinine and provides facile access to complex sulfur-containing compounds with three contiguous stereogenic centers in yields of up to 93%, with 95:5 dr and 95% ee. These compounds were further elaborated to give the equivalent of a chiral aza-Morita-Baylis-Hillman reaction involving chalcones and azetidines bearing four chiral centers.