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

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

2023Organic Letters36 citationsDOI

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.

Topics & Concepts

AnnulationChemistryCatalysisCombinatorial chemistryAxial symmetryElectrochemistryCobaltOxygen atomMoleculeStereochemistryOrganic chemistryPhysical chemistryElectrodeStructural engineeringEngineeringAxial and Atropisomeric Chirality SynthesisMolecular spectroscopy and chiralitySphingolipid Metabolism and Signaling
C–N Axially Chiral Heterobiaryl Isoquinolinone Skeletons Construction via Cobalt-Catalyzed Atroposelective C–H Activation/Annulation | Litcius