Asymmetric catalysis mediated by a mirror symmetry-broken helical nanoribbon

Zhaocun Shen (), Yutao Sang, Tianyu Wang, Jian Jiang, Yan Meng, Yuqian Jiang, Kou Okuro (), Takuzo Aida () and Minghua Liu ()
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Zhaocun Shen: CAS Research/Education Center for Excellence in Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences
Yutao Sang: CAS Research/Education Center for Excellence in Molecular Sciences, Institute of Chemistry, 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
Yuqian Jiang: National Center for Nanoscience and Technology
Kou Okuro: The University of Tokyo
Takuzo Aida: The University of Tokyo
Minghua Liu: CAS Research/Education Center for Excellence in Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences

Nature Communications, 2019, vol. 10, issue 1, 1-8

Abstract: 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.

Date: 2019
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DOI: 10.1038/s41467-019-11840-3

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