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Asymmetric catalysis mediated by a mirror symmetry-broken helical nanoribbon

Author

Listed:
  • Zhaocun Shen

    (CAS Research/Education Center for Excellence in Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences
    The University of Tokyo
    University of Chinese Academy of Sciences)

  • Yutao Sang

    (CAS Research/Education Center for Excellence in Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences
    University of Chinese Academy of Sciences)

  • Tianyu Wang

    (CAS Research/Education Center for Excellence in Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences)

  • Jian Jiang

    (National Center for Nanoscience and Technology)

  • Yan Meng

    (CAS Research/Education Center for Excellence in Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences
    University of Chinese Academy of Sciences)

  • Yuqian Jiang

    (National Center for Nanoscience and Technology)

  • Kou Okuro

    (The University of Tokyo)

  • Takuzo Aida

    (The University of Tokyo
    RIKEN Center for Emergent Matter Science)

  • Minghua Liu

    (CAS Research/Education Center for Excellence in Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences
    University of Chinese Academy of Sciences
    National Center for Nanoscience and Technology
    Collaborative Innovation Center of Chemical Science and Engineering)

Abstract

Although chirality has been recognized as an essential entity for life, it still remains a big mystery how the homochirality in nature emerged in essential biomolecules. Certain achiral motifs are known to assemble into chiral nanostructures. In rare cases, their absolute geometries are enantiomerically biased by mirror symmetry breaking. Here we report the first example of asymmetric catalysis by using a mirror symmetry-broken helical nanoribbon as the ligand. We obtain this helical nanoribbon from a benzoic acid appended achiral benzene-1,3,5-tricarboxamide by its helical supramolecular assembly and employ it for the Cu2+-catalyzed Diels–Alder reaction. By thorough optimization of the reaction (conversion: > 99%, turnover number: ~90), the enantiomeric excess eventually reaches 46% (major/minor enantiomers = 73/27). We also confirm that the helical nanoribbon indeed carries helically twisted binding sites for Cu2+. Our achievement may provide the fundamental breakthrough for producing optically active molecules from a mixture of totally achiral motifs.

Suggested Citation

  • Zhaocun Shen & Yutao Sang & Tianyu Wang & Jian Jiang & Yan Meng & Yuqian Jiang & Kou Okuro & Takuzo Aida & Minghua Liu, 2019. "Asymmetric catalysis mediated by a mirror symmetry-broken helical nanoribbon," Nature Communications, Nature, vol. 10(1), pages 1-8, December.
    • Handle: RePEc:nat:natcom:v:10:y:2019:i:1:d:10.1038_s41467-019-11840-3
    DOI: 10.1038/s41467-019-11840-3
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    Cited by:

    1. Ran Chen & Ahmad Hammoud & Paméla Aoun & Mayte A. Martínez-Aguirre & Nicolas Vanthuyne & Régina Maruchenko & Patrick Brocorens & Laurent Bouteiller & Matthieu Raynal, 2024. "Switchable supramolecular helices for asymmetric stereodivergent catalysis," Nature Communications, Nature, vol. 15(1), pages 1-11, December.

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