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通过卡宾对芳烃C-H键的不对称插入构建C-C轴手性

Construction of C-C Axial Chirality via Asymmetric Carbene Insertion into Arene C-H Bonds.

作者信息

Li Ziyong, Chen Ying, Wang Chuang, Xu Guangyang, Shao Ying, Zhang Xinhao, Tang Shengbiao, Sun Jiangtao

机构信息

Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, School of Petrochemical Engineering, Changzhou University, 1 Gehu Road, 213164, Changzhou, China.

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

出版信息

Angew Chem Int Ed Engl. 2021 Dec 1;60(49):25714-25718. doi: 10.1002/anie.202110430. Epub 2021 Nov 3.

DOI:10.1002/anie.202110430
PMID:34597448
Abstract

By using diazonaphthoquinones and anilines as key reagents and through a point-to-axis chiral transfer strategy, the atroposelective synthesis via asymmetric C(sp )-H bond insertion reaction of arenes has been realized under rhodium catalysis, providing the resulting biaryl atropisomers in moderate to excellent yields with good enantiomeric ratios (up to 99:1). Further elaboration indicates this type of axially biaryl scaffold may have promising potentials in developing novel chiral ligands.

摘要

通过使用重氮萘醌和苯胺作为关键试剂,并通过点到轴的手性转移策略,在铑催化下实现了芳烃的不对称C(sp )-H键插入反应的轴手性选择性合成,以中等至优异的产率和良好的对映体比例(高达99:1)提供了所得的联芳基轴手性异构体。进一步的研究表明,这种类型的轴手性联芳基支架在开发新型手性配体方面可能具有广阔的潜力。

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