N-Heterocyclic carbene-catalyzed enantioselective synthesis of planar-chiral cyclophanes via dynamic kinetic resolution

Jiayan Li, Ziyang Dong, Yang Chen, Zhanhui Yang, Xinen Yan, Meng Wang, Chenyang Li () and Changgui Zhao ()
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Jiayan Li: Beijing Normal University
Ziyang Dong: Beijing Normal University
Yang Chen: Beijing University of Chemical Technology
Zhanhui Yang: Beijing University of Chemical Technology
Xinen Yan: Beijing Normal University
Meng Wang: Beijing Normal University
Chenyang Li: Beijing Normal University
Changgui Zhao: Beijing Normal University

Nature Communications, 2024, vol. 15, issue 1, 1-11

Abstract: Abstract Planar-chiral cyclophanes have gained considerable concerns for drug discovery due to their unique conformational strain and 3D structure. However, the enantioselective synthesis of planar-chiral cyclophanes is a long-standing challenge for the synthetic community. We herein describe an N-heterocyclic carbene (NHC)-catalyzed asymmetric construction of planar-chiral cyclophanes. This transformation occurs through a dynamic kinetic resolution (DKR) process to convert racemic substrates into planar-chiral macrocycle scaffolds in good to high yields with high to excellent enantioselectivities. The ansa chain length and aromatic ring substituent size is crucial to achieve the DKR approach. Controlled experiments and DFT calculations were performed to clarify the DKR process.

Date: 2024
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DOI: 10.1038/s41467-024-46376-8

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