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通过不对称铑催化的双C-H活化对映选择性合成C-N轴手性N-芳基氧化吲哚

Enantioselective Synthesis of C-N Axially Chiral N-Aryloxindoles by Asymmetric Rhodium-Catalyzed Dual C-H Activation.

作者信息

Li Honghe, Yan Xiaoqiang, Zhang Jitan, Guo Weicong, Jiang Jijun, Wang Jun

机构信息

Key Laboratory of Bioinorganic and Synthetic Chemistry of Ministry of Education, School of Chemistry, Sun Yat-Sen University, Guangzhou, 510275, P. R. China.

出版信息

Angew Chem Int Ed Engl. 2019 May 13;58(20):6732-6736. doi: 10.1002/anie.201901619. Epub 2019 Apr 9.

DOI:10.1002/anie.201901619
PMID:30893497
Abstract

The first enantioselective Satoh-Miura-type reaction is reported. A variety of C-N axially chiral N-aryloxindoles have been enantioselectively synthesized by an asymmetric rhodium-catalyzed dual C-H activation reaction of N-aryloxindoles and alkynes. High yields and enantioselectivities were obtained (up to 99 % yield and up to 99 % ee). To date, it is also the first example of the asymmetric synthesis of C-N axially chiral compounds by such a C-H activation strategy.

摘要

报道了首例对映选择性的佐藤-三浦型反应。通过铑催化的N-芳基氧化吲哚与炔烃的不对称双C-H活化反应,对映选择性地合成了多种C-N轴手性N-芳基氧化吲哚。反应获得了高产率和对映选择性(产率高达99%,对映体过量值高达99%)。迄今为止,这也是通过这种C-H活化策略对映选择性合成C-N轴手性化合物的首例。

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