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Catalytic synthesis of chiral sulfinimidate esters via oxidative esterification of sulfenamides

Author

Listed:
  • Hua-Jie Jiang

    (Anhui Agricultural University
    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
    Anhui Agricultural University)

  • Jie Yu

    (Anhui Agricultural University
    Anhui Agricultural University)

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.

Suggested Citation

  • Hua-Jie Jiang & Xue-Qin Tu & Xin-Yi Kong & Ju-Yan Wang & Yu-Yang Liu & Meng-Lan Shen & Chuan-Zhi Yao & Qiankun Li & Jie Yu, 2025. "Catalytic synthesis of chiral sulfinimidate esters via oxidative esterification of sulfenamides," Nature Communications, Nature, vol. 16(1), pages 1-8, December.
    • Handle: RePEc:nat:natcom:v:16:y:2025:i:1:d:10.1038_s41467-025-62197-9
    DOI: 10.1038/s41467-025-62197-9
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    References listed on IDEAS

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    1. Christopher Lipinski & Andrew Hopkins, 2004. "Navigating chemical space for biology and medicine," Nature, Nature, vol. 432(7019), pages 855-861, December.
    2. Jiahui Xue & Xuefeng Jiang, 2020. "Unsymmetrical polysulfidation via designed bilateral disulfurating reagents," Nature Communications, Nature, vol. 11(1), pages 1-8, December.
    3. Bing-Bing Sun & Kun Liu & Quan Gao & Wei Fang & Shuang Lu & Chun-Ru Wang & Chuan-Zhi Yao & Hai-Qun Cao & Jie Yu, 2022. "Enantioselective Ugi and Ugi-azide reactions catalyzed by anionic stereogenic-at-cobalt(III) complexes," Nature Communications, Nature, vol. 13(1), pages 1-11, December.
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