Catalytic asymmetric synthesis of planar-chiral dianthranilides via (Dynamic) kinetic resolution

Chun-Yan Guan, Shuai Zou, Can Luo, Zhen-Yu Li, Mingjie Huang, Lihua Huang (), Xiao Xiao, Donghui Wei, Min-Can Wang and Guang-Jian Mei ()
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Chun-Yan Guan: Zhengzhou University
Shuai Zou: Zhengzhou University
Can Luo: Zhengzhou University
Zhen-Yu Li: Zhengzhou University
Mingjie Huang: Zhengzhou University
Lihua Huang: Zhengzhou University
Xiao Xiao: Zhejiang University of Technology
Donghui Wei: Zhengzhou University
Min-Can Wang: Zhengzhou University
Guang-Jian Mei: Zhengzhou University

Nature Communications, 2024, vol. 15, issue 1, 1-10

Abstract: Abstract Chirality constitutes an inherent attribute of nature. The catalytic asymmetric synthesis of molecules with central, axial, and helical chirality is a topic of intense interest and is becoming a mature field of research. However, due to the difficulty in synthesis and the lack of a prototype, less attention has been given to planar chirality arising from the destruction of symmetry on a single planar ring. Herein, we report the catalytic asymmetric synthesis of planar-chiral dianthranilides, a unique class of tub-shaped eight-membered cyclic dilactams. This protocol is enabled by cinchona alkaloid-catalyzed (dynamic) kinetic resolution. Under mild conditions, various C2- or C1-symmetric planar-chiral dianthranilides have been readily prepared in high yields with excellent enantioselectivity. These dianthranilides can serve as an addition to the family of planar-chiral molecules. Its synthetic value has been demonstrated by kinetic resolution of racemic amines via acyl transfer, enantiodivergent synthesis of the natural product eupolyphagin, and preliminary antitumor activity studies.

Date: 2024
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DOI: 10.1038/s41467-024-48947-1

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