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通过钴催化的阻转选择性C-H活化/环化构建C-N轴手性杂联芳基异喹啉酮骨架

C-N Axially Chiral Heterobiaryl Isoquinolinone Skeletons Construction via Cobalt-Catalyzed Atroposelective C-H Activation/Annulation.

作者信息

Wang Xinhai, Si Xiao-Ju, Sun Yingjie, Wei Zhisen, Xu Miao, Yang Dandan, Shi Linlin, Song Mao-Ping, Niu Jun-Long

机构信息

College of Chemistry, Zhengzhou University, Zhengzhou 450001, P. R. China.

出版信息

Org Lett. 2023 Sep 1;25(34):6240-6245. doi: 10.1021/acs.orglett.3c01685. Epub 2023 Aug 18.

Abstract

Herein, the atroposelective construction of isoquinolinones bearing a C-N chiral axis has been successfully developed via a Co-catalyzed C-H bond activation and annulation process. This conversion can be effectively carried out in an environmentally friendly oxygen atmosphere to generate the target C-N axially chiral frameworks with excellent reactivities and enantioselectivities (up to >99% ee) in the absence of any additives. Additionally, the current protocol has proved to be an alternative approach for the C-N axial architectures fabrication under electrochemical conditions for cobalt/Salox catalysis, and this strategy allowed the efficient and atom-economical synthesis of various axially chiral isoquinolinones under mild reaction conditions.

摘要

在此,通过钴催化的C-H键活化和环化过程,成功开发了具有C-N手性轴的异喹啉酮的对映选择性构建方法。该转化反应能够在环境友好的氧气氛围中有效进行,无需任何添加剂,即可生成具有优异反应活性和对映选择性(高达>99% ee)的目标C-N轴手性骨架。此外,目前的方法已被证明是在电化学条件下钴/水杨醛肟催化制备C-N轴结构的另一种途径,该策略能够在温和的反应条件下高效、原子经济地合成各种轴手性异喹啉酮。

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