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Skeletal reorganization divergence of N-sulfonyl ynamides

Author

Listed:
  • Linwei Zeng

    (Zhejiang University)

  • Yuxin Lin

    (Zhejiang University)

  • Jiaming Li

    (Zhejiang University)

  • Hironao Sajiki

    (Gifu Pharmaceutical University)

  • Hujun Xie

    (Zhejiang Gongshang University)

  • Sunliang Cui

    (Zhejiang University)

Abstract

Skeletal reorganization is a type of intriguing processes because of their interesting mechanism, high atom-economy and synthetic versatility. Herein, we describe an unusual, divergent skeletal reorganization of N-sulfonyl ynamides. Upon treatment with lithium diisopropylamine (LDA), N-sulfonyl ynamides undergo a skeletal reorganization to deliver thiete sulfones, while the additional use of 1,3-dimethyl-tetrahydropyrimidin-2(1H)-one (DMPU) shifts the process to furnish propargyl sulfonamides. This skeletal reorganization divergence features broad substrate scope and scalability. Mechanistically, experimental and computational studies reveal that these processes may initiate from a lithiation/4-exo-dig cyclization cascade, and the following ligand-dependent 1,3-sulfonyl migration or β-elimination would control the chemodivergence. This protocol additionally provides a facile access to a variety of privileged molecules from easily accessible ynamides.

Suggested Citation

  • 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.
    • Handle: RePEc:nat:natcom:v:11:y:2020:i:1:d:10.1038_s41467-020-19467-5
    DOI: 10.1038/s41467-020-19467-5
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    Cited by:

    1. Mohana Reddy Mutra & Jeh‐Jeng Wang, 2022. "Photoinduced ynamide structural reshuffling and functionalization," Nature Communications, Nature, vol. 13(1), pages 1-14, December.
    2. 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.

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