1. Catalytic asymmetric synthesis of planar-chiral dianthranilides via (Dynamic) kinetic resolution
- Author
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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
- Subjects
Science - 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 C 2 - or C 1 -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.
- Published
- 2024
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