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Updated: Sep 16, 2025

Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
Organocatalytic kinetic resolution of sulfinamides by N/O exchange
Xi Zou1,2,3, Xinghua Wang4, Zhaowang Duan1,2
1Institute of Drug Discovery and Design, College of Pharmaceutical Sciences, Zhejiang University, Hangzhou, Zhejiang, China.
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.
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