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Organocatalytic kinetic resolution of sulfinamides by N/O exchange

Author

Listed:
  • Xi Zou

    (Zhejiang University
    Hunan University
    Zhejiang University)

  • Xinghua Wang

    (Zhengzhou University)

  • Zhaowang Duan

    (Zhejiang University
    Hunan University)

  • Hongjian Jiao

    (Zhejiang University
    Hunan University)

  • Yu Lan

    (Zhengzhou University)

  • Xinhui Su

    (Zhejiang University)

  • Bing Gao

    (Zhejiang University
    Hunan University
    Zhejiang University)

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.

Suggested Citation

  • Xi Zou & Xinghua Wang & Zhaowang Duan & Hongjian Jiao & Yu Lan & Xinhui Su & Bing Gao, 2025. "Organocatalytic kinetic resolution of sulfinamides by N/O exchange," Nature Communications, Nature, vol. 16(1), pages 1-9, December.
    • Handle: RePEc:nat:natcom:v:16:y:2025:i:1:d:10.1038_s41467-025-61429-2
    DOI: 10.1038/s41467-025-61429-2
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    References listed on IDEAS

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    1. Xiaowu Fang & Longlong Xi & Minyan Wang & Jieshuai Xiao & Yue Zhao & Michael C. Willis & Zhuangzhi Shi, 2025. "Asymmetric reductive arylation and alkenylation to access S-chirogenic sulfinamides," Nature Communications, Nature, vol. 16(1), pages 1-10, December.
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