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Catalytic enantioselective synthesis of inherently chiral calix[4]arenes via organocatalyzed aromatic amination enabled desymmetrization

Author

Listed:
  • Mengyao Yuan

    (ShanghaiTech University
    Lingang Laboratory)

  • Wansen Xie

    (ShanghaiTech University)

  • Shaoze Yu

    (ShanghaiTech University)

  • Tong Liu

    (ShanghaiTech University)

  • Xiaoyu Yang

    (ShanghaiTech University
    Nankai University)

Abstract

Inherently chiral calix[4]arenes represent a distinct class of chiral frameworks whose chirality arises from the dissymmetry of the entire molecule. Although these chiral scaffolds have been widely applied in various research fields, their catalytic enantioselective synthesis remains largely underexplored. Herein, we report the enantioselective synthesis of inherently chiral calix[4]arenes using an organocatalyzed desymmetrization method. By using chiral phosphoric acid catalysis, the asymmetric electrophilic amination reactions of the phenol-containing prochiral calix[4]arenes led to a range of inherently chiral calix[4]arenes with high yields and enantioselectivities. Significantly, the practicability of this method is underscored by its successful implementation using as little as 0.05 mol% of chiral catalyst, without compromising reaction efficiency and enantioselectivity. Moreover, the aminophenol moiety in the products could be easily modified to produce unique calix[4]arenes with diverse N,O-heterocycles, as well as the simple meta-amino-substituted chiral calix[4]arene, which have shown promising potential in the development of new chiral catalysts.

Suggested Citation

  • Mengyao Yuan & Wansen Xie & Shaoze Yu & Tong Liu & Xiaoyu Yang, 2025. "Catalytic enantioselective synthesis of inherently chiral calix[4]arenes via organocatalyzed aromatic amination enabled desymmetrization," Nature Communications, Nature, vol. 16(1), pages 1-11, December.
  • Handle: RePEc:nat:natcom:v:16:y:2025:i:1:d:10.1038_s41467-025-59221-3
    DOI: 10.1038/s41467-025-59221-3
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    References listed on IDEAS

    as
    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. 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.
    3. Tong Li & Yanbo Zhang & Cong Du & Dandan Yang & Mao-Ping Song & Jun-Long Niu, 2024. "Simultaneous construction of inherent and axial chirality by cobalt-catalyzed enantioselective C-H activation of calix[4]arenes," Nature Communications, Nature, vol. 15(1), pages 1-10, December.
    4. Zi-Lei Xia & Chao Zheng & Ren-Qi Xu & Shu-Li You, 2019. "Chiral phosphoric acid catalyzed aminative dearomatization of α-naphthols/Michael addition sequence," Nature Communications, Nature, vol. 10(1), pages 1-7, December.
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