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金与磷酸协同催化实现重氮酯与苯甲醚的不对称芳基化反应

Asymmetric Arylation of Diazoesters with Anisoles Enabled by Cooperative Gold and Phosphoric Acid Catalysis.

作者信息

Xu Guangyang, Huang Meirong, Zhang Tao, Shao Ying, Tang Shengbiao, Cao He, Zhang Xinhao, Sun Jiangtao

机构信息

School of Petrochemical Engineering, Changzhou University, Changzhou, Jiangsu 213164, China.

Shenzhen Bay Laboratory, State Key Laboratory of Chemical Oncogeomics, Peking University Shenzhen Graduate School, Shenzhen, Guangdong 518055, China.

出版信息

Org Lett. 2022 Apr 22;24(15):2809-2814. doi: 10.1021/acs.orglett.2c00709. Epub 2022 Apr 8.

Abstract

An enantioselective insertion of a carbene into the Csp-H bond of anisole derivatives has been accomplished using an achiral gold complex and a chiral phosphoric acid as the catalytic system, providing a novel protocol for the synthesis of chiral α,α-diaryl acetates. Density functional theory calculations reveal the reactivity and the origin of the enantioselectivity of this reaction.

摘要

使用非手性金配合物和手性磷酸作为催化体系,实现了卡宾对苯甲醚衍生物Csp-H键的对映选择性插入反应,为手性α,α-二芳基乙酸酯的合成提供了一种新方法。密度泛函理论计算揭示了该反应的反应活性和对映选择性的起源。

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