Simultaneous construction of inherent and axial chirality by cobalt-catalyzed enantioselective C-H activation of calix[4]arenes

Tong Li, Yanbo Zhang, Cong Du, Dandan Yang (), Mao-Ping Song and Jun-Long Niu ()
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Tong Li: Zhengzhou University
Yanbo Zhang: Zhengzhou University
Cong Du: Henan University
Dandan Yang: Zhengzhou University
Mao-Ping Song: Zhengzhou University
Jun-Long Niu: Zhengzhou University

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

Abstract: Abstract The simultaneous construction of multiple stereogenic elements in a single step is highly appealing and desirable in the field of asymmetric synthesis. Furthermore, the catalytic enantioselective synthesis of inherently chiral calix[n]arenes with high enantiopurity has long been a challenging endeavor. Herein, we report an enantioselective cobalt-catalyzed C–H activation/annulation for the efficient construction of inherently chiral calix[4]arenes bearing multiple C–N axially chiral element. By employing the benzamide tethered calix[4]arene as the substrate, the C–H annulation with alkynes can be successfully accomplished, leading to the generation of multiple stereogenic elements. A wide range of calix[4]arenes and alkynes are found to be well compatible, and exhibit good yields, high enantioselectivity and excellent diastereoselectivity. Notably, the gram-scale reaction, catalytic application, synthetic transformations, and chiral recognition further showcase the potential applications of this protocol.

Date: 2024
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DOI: 10.1038/s41467-024-52133-8

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