Organocatalytic kinetic resolution of sulfinamides by N/O exchange

Xi Zou, Xinghua Wang, Zhaowang Duan, Hongjian Jiao, Yu Lan (), Xinhui Su () and Bing Gao ()
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Xi Zou: Zhejiang University
Xinghua Wang: Zhengzhou University
Zhaowang Duan: Zhejiang University
Hongjian Jiao: Zhejiang University
Yu Lan: Zhengzhou University
Xinhui Su: Zhejiang University
Bing Gao: Zhejiang University

Nature Communications, 2025, vol. 16, issue 1, 1-9

Abstract: Abstract Kinetic resolution is a promising strategy for accessing enantioenriched molecules from racemic mixtures. However, this method has not previously been realized in the synthesis of chiral sulfinyl scaffolds via S(IV)−X bond exchange. We disclose a kinetic resolution reaction of sulfinamides with alcohols in this report. It affords sulfinate esters and enantioenriched sulfinamides with high enantioselectivity across a broad substrate scope. These two products serve as versatile chiral sulfinyl reagents, enabling further transformation into diverse functional molecules. Mechanistic studies suggest a dual activation transition state, wherein both the sulfinamide and alcohol substrates are engaged by a squaramide catalyst through hydrogen-bonding interactions. This method offers a mechanistic and synthetic complement to established dynamic asymmetric processes for constructing chiral sulfinyl frameworks.

Date: 2025
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DOI: 10.1038/s41467-025-61429-2

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