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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.
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1 Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Colloid, Interface and Chemical Thermodynamics, CAS Research/Education Center for Excellence in Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing, P. R. China; Department of Chemistry and Biotechnology, School of Engineering, The University of Tokyo, Tokyo, Japan; University of Chinese Academy of Sciences, Beijing, P. R. China
2 Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Colloid, Interface and Chemical Thermodynamics, CAS Research/Education Center for Excellence in Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing, P. R. China; University of Chinese Academy of Sciences, Beijing, P. R. China
3 Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Colloid, Interface and Chemical Thermodynamics, CAS Research/Education Center for Excellence in Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing, P. R. China
4 CAS Center for Excellence in Nanoscience, National Center for Nanoscience and Technology, Beijing, P. R. China
5 Department of Chemistry and Biotechnology, School of Engineering, The University of Tokyo, Tokyo, Japan
6 Department of Chemistry and Biotechnology, School of Engineering, The University of Tokyo, Tokyo, Japan; RIKEN Center for Emergent Matter Science, Saitama, Japan
7 Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Colloid, Interface and Chemical Thermodynamics, CAS Research/Education Center for Excellence in Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing, P. R. China; University of Chinese Academy of Sciences, Beijing, P. R. China; CAS Center for Excellence in Nanoscience, National Center for Nanoscience and Technology, Beijing, P. R. China; Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, P. R. China