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铜(I)催化的胺、炔烃和烯酮的[2 + 2 + 1]环加成反应:全取代β-吡咯烷酮的反转和区域选择性方法。

Cu(I)-Catalyzed [2 + 2 + 1] Cycloaddition of Amines, Alkynes, and Ketenes: An Umpolung and Regioselective Approach to Full-Substituted β-Pyrrolinones.

机构信息

Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Henan Key Laboratory of Organic Functional Molecule and Drug Innovation, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China.

State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road 38, Beijing 100191, China.

出版信息

Org Lett. 2021 Feb 5;23(3):762-766. doi: 10.1021/acs.orglett.0c03991. Epub 2021 Jan 14.

Abstract

Described here is a Cu-catalyzed [2 + 2 + 1] modular synthesis of full-substituted β-pyrrolinones from simple amines, alkynes, and α-diazo-β-ketoesters. This approach involving the regioselective C-nucleophilic attack of enamines, uncommon C-nucleophilic addition to ketenes, and umpolung of imines enables the direct synthesis of full-substituted β-pyrrolinones, which were hardly constructed by traditional synthetic strategies.

摘要

这里描述了一种铜催化的[2 + 2 + 1]模块化合成全取代β-吡咯烷酮的方法,该方法使用简单的胺、炔烃和α-重氮-β-酮酯。该方法涉及烯胺的区域选择性 C-亲核进攻、酮烯的不常见的 C-亲核加成以及亚胺的反转,能够直接合成全取代的β-吡咯烷酮,而这些化合物很难通过传统的合成策略构建。

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