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Organocatalyzed diastereo- and enantioselective synthesis of N–N atropisomeric isoindolinones bearing central chirality

Author

Listed:
  • Xingguang Li

    (East China University of Science and Technology)

  • Xin-Ze Wang

    (East China University of Science and Technology)

  • Boming Shen

    (Southern University of Science and Technology)

  • Qian-Yu Chen

    (East China University of Science and Technology)

  • Huijing Xiang

    (Shanghai University)

  • Peiyuan Yu

    (Southern University of Science and Technology)

  • Pei-Nian Liu

    (East China University of Science and Technology
    China Pharmaceutical University)

Abstract

Methods for catalytically constructing of N–N axially chiral scaffolds have garnered significant attention since such compounds are widely present in natural products, bioactive molecules, and organic materials. Herein, we report a highly diastereoselective and enantioselective organocatalyzed [4 + 1] annulation method for synthesizing diverse valuable isoindolinones that possessing N–N axial and central chiralities. This methodology uses a chiral phosphoric acid as a bifunctional catalyst to promote a cascade sequence involving two nucleophilic additions, dehydration, and dearomatization processes. Control experiments and DFT calculations revealed a possible mechanism in which the stereoselectivity-determining step is likely to involve the irreversible formation of a hydroxy biaryl intermediate. Additionally, preliminary biological activity studies showed that some of these N–N axially chiral isoindolinones have potential in suppressing tumor-cell proliferation.

Suggested Citation

  • Xingguang Li & Xin-Ze Wang & Boming Shen & Qian-Yu Chen & Huijing Xiang & Peiyuan Yu & Pei-Nian Liu, 2025. "Organocatalyzed diastereo- and enantioselective synthesis of N–N atropisomeric isoindolinones bearing central chirality," Nature Communications, Nature, vol. 16(1), pages 1-11, December.
  • Handle: RePEc:nat:natcom:v:16:y:2025:i:1:d:10.1038_s41467-025-56838-2
    DOI: 10.1038/s41467-025-56838-2
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    References listed on IDEAS

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    1. Yishou Wang & Xiaohan Zhu & Deng Pan & Jierui Jing & Fen Wang & Ruijie Mi & Genping Huang & Xingwei Li, 2023. "Rhodium-catalyzed enantioselective and diastereodivergent access to diaxially chiral heterocycles," Nature Communications, Nature, vol. 14(1), pages 1-12, December.
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