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Enantioselective synthesis of chiral quinohelicenes through sequential organocatalyzed Povarov reaction and oxidative aromatization

Author

Listed:
  • Chengwen Li

    (Nankai University)

  • Ying-Bo Shao

    (Nankai University)

  • Xi Gao

    (Nankai University)

  • Zhiyuan Ren

    (Nankai University)

  • Chenhao Guo

    (Chinese Academy of Sciences)

  • Meng Li

    (Chinese Academy of Sciences)

  • Xin Li

    (Nankai University
    Haihe Laboratory of Sustainable Chemical Transformations)

Abstract

Heterohelicenes are of increasing importance in the fields of materials science, molecular recognition, and asymmetric catalysis. However, enantioselective construction of these molecules, especially by organocatalytic methods, is challenging, and few methods are available. In this study, we synthesize enantioenriched 1-(3-indol)-quino[n]helicenes through chiral phosphoric acid-catalyzed Povarov reaction followed by oxidative aromatization. The method has a broad substrate scope and offers rapid access to an array of chiral quinohelicenes with enantioselectivities up to 99%. Additionally, the photochemical and electrochemical properties of selected quinohelicenes are explored.

Suggested Citation

  • Chengwen Li & Ying-Bo Shao & Xi Gao & Zhiyuan Ren & Chenhao Guo & Meng Li & Xin Li, 2023. "Enantioselective synthesis of chiral quinohelicenes through sequential organocatalyzed Povarov reaction and oxidative aromatization," Nature Communications, Nature, vol. 14(1), pages 1-9, December.
    • Handle: RePEc:nat:natcom:v:14:y:2023:i:1:d:10.1038_s41467-023-39134-9
    DOI: 10.1038/s41467-023-39134-9
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    References listed on IDEAS

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    1. Yunchang Liang & Karla Banjac & Kévin Martin & Nicolas Zigon & Seunghwa Lee & Nicolas Vanthuyne & Felipe Andrés Garcés-Pineda & José R. Galán-Mascarós & Xile Hu & Narcis Avarvari & Magalí Lingenfelder, 2022. "Enhancement of electrocatalytic oxygen evolution by chiral molecular functionalization of hybrid 2D electrodes," Nature Communications, Nature, vol. 13(1), pages 1-9, December.
    2. Chengshuo Shen & Guoli Zhang & Yongle Ding & Na Yang & Fuwei Gan & Jeanne Crassous & Huibin Qiu, 2021. "Oxidative cyclo-rearrangement of helicenes into chiral nanographenes," Nature Communications, Nature, vol. 12(1), pages 1-8, December.
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    Cited by:

    1. Xihong Liu & Boyan Zhu & Xiaoyong Zhang & Hanwen Zhu & Jingying Zhang & Anqi Chu & Fujun Wang & Rui Wang, 2024. "Enantioselective synthesis of [4]helicenes by organocatalyzed intermolecular C-H amination," Nature Communications, Nature, vol. 15(1), pages 1-12, December.
    2. Jiahao Wu & Xiangwen Tan & Wanqing Wu & Huanfeng Jiang, 2024. "Palladium-catalyzed cascade of aza-Wacker and Povarov reactions of aryl amines and 1,6-dienes for hexahydro-cyclopenta[b]quinoline framework," Nature Communications, Nature, vol. 15(1), pages 1-11, December.

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