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Asymmetric Büchner reaction and arene cyclopropanation via copper-catalyzed controllable cyclization of diynes

Author

Listed:
  • Yan-Xin Zheng

    (Xiamen University)

  • Li-Gao Liu

    (Zhejiang University)

  • Tian-Qi Hu

    (Xiamen University)

  • Xiao Li

    (Xiamen University)

  • Zhou Xu

    (Xuzhou Medical University)

  • Xin Hong

    (Xiamen University
    Zhejiang University)

  • Xin Lu

    (Xiamen University)

  • Bo Zhou

    (Xiamen University)

  • Long-Wu Ye

    (Xiamen University
    Chinese Academy of Sciences)

Abstract

The asymmetric Büchner reaction and related arene cyclopropanations represent one type of the powerful methods for enantioselective dearomatization. However, examples of asymmetric Büchner reactions via a non-diazo approach are quite scarce, and the related arene cyclopropanation based on alkynes has not been reported. Herein, we disclose an asymmetric Büchner reaction and the related arene cyclopropanation by copper-catalyzed controllable cyclization of N-propargyl ynamides via vinyl cation intermediates, leading to chiral tricycle-fused cycloheptatrienes and benzonorcaradienes in high yields and enantioselectivities. Importantly, this protocol represents an asymmetric arene cyclopropanation reaction of alkynes and an asymmetric Büchner reaction based on vinyl cations.

Suggested Citation

  • Yan-Xin Zheng & Li-Gao Liu & Tian-Qi Hu & Xiao Li & Zhou Xu & Xin Hong & Xin Lu & Bo Zhou & Long-Wu Ye, 2024. "Asymmetric Büchner reaction and arene cyclopropanation via copper-catalyzed controllable cyclization of diynes," Nature Communications, Nature, vol. 15(1), pages 1-13, December.
    • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-53605-7
    DOI: 10.1038/s41467-024-53605-7
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    References listed on IDEAS

    as
    1. Cui-Ting Li & Lin-Jun Qi & Li-Gao Liu & Chang Ge & Xin Lu & Long-Wu Ye & Bo Zhou, 2023. "Asymmetric formal C–C bond insertion into aldehydes via copper-catalyzed diyne cyclization," Nature Communications, Nature, vol. 14(1), pages 1-10, December.
    2. Yang-Bo Chen & Li-Gao Liu & Zhe-Qi Wang & Rong Chang & Xin Lu & Bo Zhou & Long-Wu Ye, 2024. "Enantioselective functionalization of unactivated C(sp3)–H bonds through copper-catalyzed diyne cyclization by kinetic resolution," Nature Communications, Nature, vol. 15(1), pages 1-10, December.
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