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Organocatalytic skeletal reorganization for enantioselective synthesis of S-stereogenic sulfinamides

Author

Listed:
  • Zanjiao Liu

    (Sichuan University)

  • Siqiang Fang

    (Sichuan University)

  • Haoze Li

    (Sichuan University)

  • Chunxiu Xiao

    (Sichuan University)

  • Kai Xiao

    (Sichuan University)

  • Zhishan Su

    (Sichuan University)

  • Tianli Wang

    (Sichuan University
    Beijing National Laboratory for Molecular Sciences)

Abstract

The enantioselective synthesis of S-stereogenic sulfinamides has garnered considerable attention due to their structural and physicochemical properties. However, catalytic asymmetric synthesis of sulfinamides still remains daunting challenges, impeding their broad application in drug discovery and development. Here, we present an approach for the synthesis of S-stereogenic sulfinamides through peptide-mimic phosphonium salt-catalyzed asymmetric skeletal reorganization of simple prochiral and/or racemic sulfoximines. This methodology allows for the facile access to a diverse array of substituted sulfinamides with excellent enantioselectivities, accommodating various substituent patterns through desymmetrization or parallel kinetic resolution process. Mechanistic experiments, coupled with density functional theory calculations, clarify a stepwise pathway involving ring-opening and ring-closing processes, with the ring-opening step identified as crucial for achieving stereoselective control. Given the prevalence of S-stereogenic centers in pharmaceuticals, we anticipate that this protocol will enhance the efficient and precise synthesis of relevant chiral molecules and their analogs, thereby contributing to advancements in drug discovery.

Suggested Citation

  • Zanjiao Liu & Siqiang Fang & Haoze Li & Chunxiu Xiao & Kai Xiao & Zhishan Su & Tianli Wang, 2024. "Organocatalytic skeletal reorganization for enantioselective synthesis of S-stereogenic sulfinamides," Nature Communications, Nature, vol. 15(1), pages 1-10, December.
  • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-48727-x
    DOI: 10.1038/s41467-024-48727-x
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    References listed on IDEAS

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    1. Warren R.J.D. Galloway & Albert Isidro-Llobet & David R. Spring, 2010. "Diversity-oriented synthesis as a tool for the discovery of novel biologically active small molecules," Nature Communications, Nature, vol. 1(1), pages 1-13, December.
    2. Jian-Ping Tan & Kehan Li & Boming Shen & Cheng Zhuang & Zanjiao Liu & Kai Xiao & Peiyuan Yu & Bing Yi & Xiaoyu Ren & Tianli Wang, 2022. "Asymmetric synthesis of N-bridged [3.3.1] ring systems by phosphonium salt/Lewis acid relay catalysis," Nature Communications, Nature, vol. 13(1), pages 1-12, December.
    3. Linwei Zeng & Yuxin Lin & Jiaming Li & Hironao Sajiki & Hujun Xie & Sunliang Cui, 2020. "Skeletal reorganization divergence of N-sulfonyl ynamides," Nature Communications, Nature, vol. 11(1), pages 1-10, December.
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