Issue 20, 2023
From the journal:

Organic Chemistry Frontiers

Kinetic resolution of heterobiaryl N-oxides by asymmetric C–H olefination: an expeditious access to (R)-QUINAP†

Qi-Ying Zhang,‡*a   Hai-Yang Wang,‡a   Songlin Wang,a   Jing Maa  and  Hai-Ming Guo ORCID logo *a  

* Corresponding authors

a State Key Laboratory of Antiviral Drugs, Pingyuan Laboratory, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China
E-mail: Zhangqiying@htu.edu.cn, ghm@htu.edu.cn

Abstract

A highly efficient kinetic resolution of heterobiaryl N-oxides was realized through Pd catalyzed-asymmetric C–H olefination with the s factor of up to 102.7. This new approach offers versatile access to two types of optically active 1-arylisoquinoline N-oxides with excellent ee (up to 97% ee and 99% ee, respectively). Moreover, the recovered arylisoquinoline N-oxides could be transformed into (R)-QUINAP with 92% ee without an external reductant in two steps.

Graphical abstract: Kinetic resolution of heterobiaryl N-oxides by asymmetric C–H olefination: an expeditious access to (R)-QUINAP

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Article information

DOI
https://doi.org/10.1039/D3QO01083J
Article type
Research Article
Submitted
13 Jul 2023
Accepted
02 Sep 2023
First published
05 Sep 2023

Org. Chem. Front., 2023,10, 5210-5215

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Kinetic resolution of heterobiaryl N-oxides by asymmetric C–H olefination: an expeditious access to (R)-QUINAP

Q. Zhang, H. Wang, S. Wang, J. Ma and H. Guo, Org. Chem. Front., 2023, 10, 5210 DOI: 10.1039/D3QO01083J

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