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Article: Asymmetric catalysis mediated by a mirror symmetry-broken helical nanoribbon

TitleAsymmetric catalysis mediated by a mirror symmetry-broken helical nanoribbon
Authors
Issue Date2019
Citation
Nature Communications, 2019, v. 10, n. 1, article no. 3976 How to Cite?
Abstract© 2019, The Author(s). 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.
Persistent Identifierhttp://hdl.handle.net/10722/276655
ISSN
2023 Impact Factor: 14.7
2023 SCImago Journal Rankings: 4.887
PubMed Central ID
ISI Accession Number ID

 

DC FieldValueLanguage
dc.contributor.authorShen, Zhaocun-
dc.contributor.authorSang, Yutao-
dc.contributor.authorWang, Tianyu-
dc.contributor.authorJiang, Jian-
dc.contributor.authorMeng, Yan-
dc.contributor.authorJiang, Yuqian-
dc.contributor.authorOkuro, Kou-
dc.contributor.authorAida, Takuzo-
dc.contributor.authorLiu, Minghua-
dc.date.accessioned2019-09-18T08:34:15Z-
dc.date.available2019-09-18T08:34:15Z-
dc.date.issued2019-
dc.identifier.citationNature Communications, 2019, v. 10, n. 1, article no. 3976-
dc.identifier.issn2041-1723-
dc.identifier.urihttp://hdl.handle.net/10722/276655-
dc.description.abstract© 2019, The Author(s). 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.-
dc.languageeng-
dc.relation.ispartofNature Communications-
dc.rightsThis work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.-
dc.titleAsymmetric catalysis mediated by a mirror symmetry-broken helical nanoribbon-
dc.typeArticle-
dc.description.naturepublished_or_final_version-
dc.identifier.doi10.1038/s41467-019-11840-3-
dc.identifier.pmid31484928-
dc.identifier.pmcidPMC6726595-
dc.identifier.scopuseid_2-s2.0-85071751345-
dc.identifier.hkuros318874-
dc.identifier.volume10-
dc.identifier.issue1-
dc.identifier.spagearticle no. 3976-
dc.identifier.epagearticle no. 3976-
dc.identifier.isiWOS:000483716100002-
dc.identifier.issnl2041-1723-

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