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

• Published in: Nature communications Vol. 15; no. 1; pp. 4580 - 10
• Main Authors: Guan, Chun-Yan, Zou, Shuai, Luo, Can, Li, Zhen-Yu, Huang, Mingjie, Huang, Lihua, Xiao, Xiao, Wei, Donghui, Wang, Min-Can, Mei, Guang-Jian
• Format: Journal Article
• Language: English
• Published: England Nature Publishing Group 29.05.2024; Nature Publishing Group UK; Nature Portfolio
• Subjects: Alkaloids; Amines; Antitumor activity; Asymmetric synthesis; Asymmetry; Catalysis; Chemical synthesis; Chemistry; Chirality; Enantiomers; Natural products; Symmetry
• ISSN: 2041-1723; 2041-1723
• DOI: 10.1038/s41467-024-48947-1

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 - or C -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.