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Construction of planar chiral [2,2]paracyclophanes via photoinduced cobalt-catalyzed desymmetric addition

Author

Listed:
  • Shi-Qi Liu

    (Central China Normal University)

  • Wei Xiong

    (Central China Normal University)

  • Ji-Chao Huang

    (Central China Normal University)

  • Xuan Jiang

    (Central China Normal University)

  • Wenhan Xu

    (Central China Normal University)

  • Zhihan Zhang

    (Central China Normal University
    Wuhan Institute of Photochemistry and Technology)

  • Ying Cheng

    (Central China Normal University
    Wuhan Institute of Photochemistry and Technology)

  • Liang-Qiu Lu

    (Central China Normal University
    Wuhan Institute of Photochemistry and Technology
    Chinese Academy of Sciences
    Henan Normal University)

  • Ke Gao

    (Central China Normal University
    Wuhan Institute of Photochemistry and Technology)

  • Wen-Jing Xiao

    (Central China Normal University
    Wuhan Institute of Photochemistry and Technology
    Lanzhou University)

Abstract

Planar chiral [2,2]paracyclophanes (PCPs) are widely used in materials science and asymmetric syntheses. Therefore, synthetic and material chemists have focused on the efficient and selective construction of planar chiral PCPs for decades. Herein, we present a photoinduced cobalt-catalyzed desymmetric addition of pseudo-para-diformyl and pseudo-gem-diformyl PCP, enabling the synthesis of planar chiral PCP alcohols with both planar and central chiralities. This method delivers 48 examples with yields up to 87%, diastereomeric ratios greater than 19:1, and an enantiomeric excess exceeding 99%. This protocol provides a original and efficient approach for the synthesis of planar chiral PCPs.

Suggested Citation

  • Shi-Qi Liu & Wei Xiong & Ji-Chao Huang & Xuan Jiang & Wenhan Xu & Zhihan Zhang & Ying Cheng & Liang-Qiu Lu & Ke Gao & Wen-Jing Xiao, 2025. "Construction of planar chiral [2,2]paracyclophanes via photoinduced cobalt-catalyzed desymmetric addition," Nature Communications, Nature, vol. 16(1), pages 1-13, December.
    • Handle: RePEc:nat:natcom:v:16:y:2025:i:1:d:10.1038_s41467-025-59089-3
    DOI: 10.1038/s41467-025-59089-3
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    References listed on IDEAS

    as
    1. Shaoze Yu & Hanyang Bao & Dekun Zhang & Xiaoyu Yang, 2023. "Kinetic resolution of substituted amido[2.2]paracyclophanes via asymmetric electrophilic amination," Nature Communications, Nature, vol. 14(1), pages 1-10, December.
    2. Vojtěch Dočekal & Filip Koucký & Ivana Císařová & Jan Veselý, 2024. "Organocatalytic desymmetrization provides access to planar chiral [2.2]paracyclophanes," Nature Communications, Nature, vol. 15(1), pages 1-8, December.
    3. Haohua Huo & Xiaodong Shen & Chuanyong Wang & Lilu Zhang & Philipp Röse & Liang-An Chen & Klaus Harms & Michael Marsch & Gerhard Hilt & Eric Meggers, 2014. "Asymmetric photoredox transition-metal catalysis activated by visible light," Nature, Nature, vol. 515(7525), pages 100-103, November.
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