Copper-catalysed dynamic kinetic asymmetric C−O cross-coupling to access chiral aryl oxime ethers and diaryl ethers

Mei-Ru Zhang, Hao-Ran Wang, Hui-Mei Shan, Long-Long Xi, Chuan-Jun Lu, Xiao-Man Du, Che Sun, Li-Ping Xu () and Ren-Rong Liu ()
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Mei-Ru Zhang: Qingdao University
Hao-Ran Wang: Qingdao University
Hui-Mei Shan: Shandong University
Long-Long Xi: Qingdao University
Chuan-Jun Lu: Qingdao University
Xiao-Man Du: Qingdao University
Che Sun: Qingdao University
Li-Ping Xu: Shandong University
Ren-Rong Liu: Qingdao University

Nature Communications, 2025, vol. 16, issue 1, 1-13

Abstract: Abstract Dynamic kinetic resolution (DKR) has emerged as an elegant and powerful tool for enantioselective synthesis, enabling the transformation of racemic compounds into enantiomerically enriched products with theoretically quantitative yields. Despite its widespread success, the dynamic kinetic asymmetric C−O cross-coupling has presented significant challenges and remains unexplored. In this study, we report a dynamic kinetic asymmetric C−O cross-coupling of oximes and phenols via copper/BOX-catalysed enantioselective O-arylation with diaryliodonium salts. This method efficiently produces a wide range of inherently chiral oxime ethers, as well as axially chiral styrenes, with high yields and excellent regio- and enantioselectivities. Through controlled experiments and Density Functional Theory (DFT) studies, we have elucidated the dynamic kinetic resolution process and gained insights into the origins of regio- and enantioselectivity.

Date: 2025
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DOI: 10.1038/s41467-025-57804-8

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