ArticleNature communications2022
Conformational enantiodiscrimination for asymmetric construction of atropisomers.
Article in Nature communications, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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11 citing papers in PubMed, 41 citations in OpenAlex.
- Article
- Kinetic Resolution of BINAMs by Stereoselective Copper-Catalyzed Dehydrogenative Si-N Coupling with Prochiral Dihydrosilanes.Organic letters · 2025Article
- Accurately adjusted phenothiazine conformations: reversible conformation transformation at room temperature and self-recoverable stimuli-responsive phosphorescence.Light, science & applications · 2025Article
- Nickel(II) Catalyzed Atroposelective Aerobic Oxidative Aryl-Aryl Cross-Coupling.ACS central science · 2025Article
- Overcoming the Pitfalls of Computing Reaction Selectivity from Ensembles of Transition States.The journal of physical chemistry letters · 2024Article
- Atroposelective catalysis.Nature reviews. Chemistry · 2024Review
- Copper-catalyzed atroposelective synthesis of C-O axially chiral compounds enabled by chiral 1,8-naphthyridine based ligands.Chemical science · 2024Article
- Atroposelective Synthesis of Aldehydes via Alcohol Dehydrogenase-Catalyzed Stereodivergent Desymmetrization.JACS Au · 2024Article
- Enantioselective construction of triaryl-substituted all-carbon quaternary stereocentersChemical science · 2023Article
- Syntheses and crystal structure of a (2,6-diiso-propyldi-naphtho-[2,1-Acta crystallographica. Section E, Crystallographic communications · 2023Article
- Syntheses and crystal structures of two di-naph-tho[2,1-Acta crystallographica. Section E, Crystallographic communications · 2023Article
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Authors and funding
6 authors at 1 institution in 1 country.
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No grant is acknowledged in the PubMed record.
Abstract
Molecular conformations induced by the rotation about single bonds play a crucial role in chemical transformations. Revealing the relationship between the conformations of chiral catalysts and the enantiodiscrimination is a formidable challenge due to the great difficulty in isolating the conformers. Herein, we report a chiral catalytic system composed of an achiral catalytically active unit and an axially chiral 1,1'-bi-2-naphthol (BINOL) unit which are connected via a C-O single bond. The two conformers of the catalyst induced by the rotation about the C-O bond, are determined via single-crystal X-ray diffraction and found to respectively lead to the formation of highly important axially chiral 1,1'-binaphthyl-2,2'-diamine (BINAM) and 2-amino-2'-hydroxy-1,1'-binaphthyl (NOBIN) derivatives in high yields (up to 98%), with excellent enantioselectivities (up to 98:2 e.r.) and opposite absolute configurations. The results highlight the importance of conformational dynamics of chiral catalysts in asymmetric catalysis.
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