Catalytic synthesis of chiral sulfinimidate esters via oxidative esterification of sulfenamides

Hua-Jie Jiang (), Xue-Qin Tu, Xin-Yi Kong, Ju-Yan Wang, Yu-Yang Liu, Meng-Lan Shen, Chuan-Zhi Yao, Qiankun Li and Jie Yu ()
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Hua-Jie Jiang: Anhui Agricultural University
Xue-Qin Tu: Anhui Agricultural University
Xin-Yi Kong: Anhui Agricultural University
Ju-Yan Wang: Anhui Agricultural University
Yu-Yang Liu: Anhui Agricultural University
Meng-Lan Shen: Anhui Agricultural University
Chuan-Zhi Yao: Anhui Agricultural University
Qiankun Li: Anhui Agricultural University
Jie Yu: Anhui Agricultural University

Nature Communications, 2025, vol. 16, issue 1, 1-8

Abstract: Abstract Aza-sulfur compounds, such as sulfilimines, sulfoximines, etc, are increasingly recognized as essential contributors to advancements in drug development and asymmetric synthesis. Among them, the catalytic enantioselective synthesis of sulfinimidate esters remains an uncharted and formidable challenge. Herein, we unveil an efficient enantioselective oxidative esterification of sulfenamides via chiral sulfinimidoyl iodide intermediates. Using stereogenic-at-Co(III) complexes as catalysts, this approach enables the synthesis of an extensive array of enantioenriched sulfinimidate esters (>70 examples, up to 98.5:1.5 er), offering a versatile platform for the preparation of structurally diverse aza-sulfur compounds.

Date: 2025
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DOI: 10.1038/s41467-025-62197-9

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