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Mn(I)-catalyzed sigmatropic rearrangement of β, γ-unsaturated alcohols

Author

Listed:
  • Can Yang

    (South China University of Technology)

  • Xiaoyu Zhou

    (Sun Yat-sen University)

  • Lixing Shen

    (South China University of Technology)

  • Zhuofeng Ke

    (Sun Yat-sen University)

  • Huanfeng Jiang

    (South China University of Technology)

  • Wei Zeng

    (South China University of Technology)

Abstract

Sigmatropic rearrangement provides a versatile strategy to site-selectively reorganize carbon-skeleton with high atom- and step-economy. Herein, we disclose a Mn(I)-catalyzed sigmatropic rearrangement of β, γ-unsaturated alcohols via C-C σ bond activation. A variety of α-aryl-allylic alcohols and α-aryl-propargyl alcohols could undergo in-situ 1,2- or 1,3- sigmatropic rearrangements to allow for converting to complex structural arylethyl- and arylvinyl- carbonyl compounds under a simple catalytic system. More importantly, this catalysis model can be further applied to assemble macrocyclic ketones through bimolecular [2n + 4] coupling-cyclization and monomolecular [n + 1] ring-extension. The presented skeleton rearrangement would be a useful tool complementary to the traditional molecular rearrangement.

Suggested Citation

  • Can Yang & Xiaoyu Zhou & Lixing Shen & Zhuofeng Ke & Huanfeng Jiang & Wei Zeng, 2023. "Mn(I)-catalyzed sigmatropic rearrangement of β, γ-unsaturated alcohols," Nature Communications, Nature, vol. 14(1), pages 1-10, December.
    • Handle: RePEc:nat:natcom:v:14:y:2023:i:1:d:10.1038_s41467-023-37299-x
    DOI: 10.1038/s41467-023-37299-x
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    References listed on IDEAS

    as
    1. Fengjuan Chen & Youxiang Shao & Mengke Li & Can Yang & Shi-Jian Su & Huanfeng Jiang & Zhuofeng Ke & Wei Zeng, 2021. "Photocatalyzed cycloaromatization of vinylsilanes with arylsulfonylazides," Nature Communications, Nature, vol. 12(1), pages 1-9, December.
    2. Guangfan Zheng & Yan Li & Jingjie Han & Tao Xiong & Qian Zhang, 2015. "Radical cascade reaction of alkynes with N-fluoroarylsulfonimides and alcohols," Nature Communications, Nature, vol. 6(1), pages 1-9, November.
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