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.

Chirality has long fascinated chemists, but asymmetric synthesis has largely focused on central, axial, and helical chirality to date. Here, the authors synthesize dianthranilides with planar chirality, via cinchona alkaloid-catalyzed (dynamic) kinetic resolution.

Details

Title
Catalytic asymmetric synthesis of planar-chiral dianthranilides via (Dynamic) kinetic resolution
Author
Guan, Chun-Yan 1 ; Zou, Shuai 1 ; Luo, Can 1 ; Li, Zhen-Yu 1 ; Huang, Mingjie 1 ; Huang, Lihua 2 ; Xiao, Xiao 3   VIAFID ORCID Logo  ; Wei, Donghui 1   VIAFID ORCID Logo  ; Wang, Min-Can 1 ; Mei, Guang-Jian 2   VIAFID ORCID Logo 

 Zhengzhou University, Henan Key Laboratory of Chemical Biology and Organic Chemistry, College of Chemistry, Zhengzhou, China (GRID:grid.207374.5) (ISNI:0000 0001 2189 3846) 
 Zhengzhou University, Henan Key Laboratory of Chemical Biology and Organic Chemistry, College of Chemistry, Zhengzhou, China (GRID:grid.207374.5) (ISNI:0000 0001 2189 3846); Pingyuan Laboratory (Zhengzhou University), Zhengzhou, China (GRID:grid.207374.5) (ISNI:0000 0001 2189 3846) 
 Zhejiang University of Technology, Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Hangzhou, China (GRID:grid.469325.f) (ISNI:0000 0004 1761 325X) 
Pages
4580
Publication year
2024
Publication date
2024
Publisher
Nature Publishing Group
e-ISSN
20411723
Source type
Scholarly Journal
Language of publication
English
ProQuest document ID
3061544330
Copyright
© The Author(s) 2024. This work is published under http://creativecommons.org/licenses/by/4.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.