Asymmetric catalysis mediated by a mirror symmetry-broken helical nanoribbon.

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 reache

SUBMITTER: Shen Z 

PROVIDER: S-EPMC6726595 | biostudies-literature | 2019 Sep

REPOSITORIES: biostudies-literature