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双核锌催化环戊二烯酮的不对称去对称化反应:构建含全碳季碳立体中心的官能化环戊二酮

Dinuclear Zinc-Catalyzed Asymmetric Desymmetrization of Cyclopentendiones: Access to Functional Cyclopentanediones Bearing an All-carbon Quaternary Stereocenter.

作者信息

Du Si-Si, Zhai Ying-Hui, Zhang Cui, Wang Min-Can, Jia Shi-Kun, Mei Guang-Jian, Hua Yuan-Zhao

机构信息

College of Chemistry and Institute of Green Catalysis, Zhengzhou University, No. 100, Science Road, Zhengzhou City Henan Province, 450000, P. R. China.

出版信息

Chem Asian J. 2023 Sep 15;18(18):e202300591. doi: 10.1002/asia.202300591. Epub 2023 Aug 9.

Abstract

The success in the identification of the two enantioisomeric surfaces of electrophiles by dinuclear zinc catalysts is disclosed. This protocol realizes a dinuclear zinc-cocatalyzed desymmetrization of cyclopentendiones using α-hydroxy aryl ketones as nucleophiles through Michael addition reaction. Under mild conditions, a series of functional cyclopentanediones bearing multiple stereogenic centers including an all-carbon quaternary stereocenter, were obtained in moderate to good yields with excellent stereoselectivities.

摘要

本文公开了通过双核锌催化剂成功识别亲电试剂的两个对映异构表面。该方案通过迈克尔加成反应,以α-羟基芳基酮为亲核试剂,实现了双核锌共催化的环戊烯二酮的去对称化反应。在温和条件下,获得了一系列带有多个立体中心(包括全碳季立体中心)的功能性环戊二酮,产率中等至良好,立体选择性优异。

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