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Organocatalytic asymmetric synthesis of Tröger’s bases

Author

Listed:
  • Yu-Wei Li

    (Zhengzhou University)

  • Nan-Nan Mo

    (Zhengzhou University)

  • Han Zhang

    (Zhengzhou University)

  • Jian-Xiao Wu

    (Zhengzhou University)

  • Tian-Jiao Han

    (Zhengzhou University
    Guizhou University)

  • Xiao Xiao

    (Zhejiang University of Technology)

  • Donghui Wei

    (Zhengzhou University)

  • Guang-Jian Mei

    (Zhengzhou University
    Guizhou University)

Abstract

The stereochemical course of nitrogen in tertiary amines has long been overlooked because of the low energy barriers for pyramidal inversion between nitrogen-based conformers. Tröger’s base (TB) is a textbook three-dimensional (3D) molecule with N-centered chirality. Despite the major development of TB chemistry, surprisingly few general strategies are available to access enantioenriched TBs. Here, we report the organocatalytic asymmetric synthesis of TBs via the aminalization of tetrahydrodibenzodiazocines with aromatic aldehydes. This chiral phosphoric acid (CPA)-catalyzed protocol features a broad substrate scope (55 examples), high efficiency (up to 96% yield), and excellent enantioselectivity (up to >99% ee). Density functional theory (DFT) calculations are performed to reveal the reaction mechanism and the origin of the enantioselectivity. The success in preparing TB-polymers and aggregation-induced emission luminogen (AIEgen) demonstrates the potential for widespread applications, especially in the fields of materials science.

Suggested Citation

  • Yu-Wei Li & Nan-Nan Mo & Han Zhang & Jian-Xiao Wu & Tian-Jiao Han & Xiao Xiao & Donghui Wei & Guang-Jian Mei, 2025. "Organocatalytic asymmetric synthesis of Tröger’s bases," Nature Communications, Nature, vol. 16(1), pages 1-13, December.
    • Handle: RePEc:nat:natcom:v:16:y:2025:i:1:d:10.1038_s41467-025-61772-4
    DOI: 10.1038/s41467-025-61772-4
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    References listed on IDEAS

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    1. Yun-Dong Fu & Han Zhang & Bei-Bei Li & Lihua Huang & Xiao Xiao & Min-Can Wang & Donghui Wei & Guang-Jian Mei, 2024. "Azocarboxamide-enabled enantioselective regiodivergent unsymmetrical 1,2-diaminations," Nature Communications, Nature, vol. 15(1), pages 1-12, December.
    2. Xiang Gao & Tian-Jiao Han & Bei-Bei Li & Xiao-Xiao Hou & Yuan-Zhao Hua & Shi-Kun Jia & Xiao Xiao & Min-Can Wang & Donghui Wei & Guang-Jian Mei, 2023. "Catalytic asymmetric dearomatization of phenols via divergent intermolecular (3 + 2) and alkylation reactions," Nature Communications, Nature, vol. 14(1), pages 1-9, December.
    3. Chun-Yan Guan & Shuai Zou & Can Luo & Zhen-Yu Li & Mingjie Huang & Lihua Huang & Xiao Xiao & Donghui Wei & Min-Can Wang & Guang-Jian Mei, 2024. "Catalytic asymmetric synthesis of planar-chiral dianthranilides via (Dynamic) kinetic resolution," Nature Communications, Nature, vol. 15(1), pages 1-10, December.
    4. Mark P. Walsh & Joseph M. Phelps & Marc E. Lennon & Dmitry S. Yufit & Matthew O. Kitching, 2021. "Enantioselective synthesis of ammonium cations," Nature, Nature, vol. 597(7874), pages 70-76, September.
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