ArticleJournal of the American Chemical Society2016
Symmetry in Cascade Chirality-Transfer Processes: A Catalytic Atroposelective Direct Arylation Approach to BINOL Derivatives.
Article in Journal of the American Chemical Society, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 23 papers.
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Who cites it
23 citing papers in PubMed.
- Recent advances in organocatalytic atroposelective reactions.Beilstein journal of organic chemistry · 2025Review
- Desymmetrization of ProchiralMolecules (Basel, Switzerland) · 2023Article
- Role of Cinchona Alkaloids in the Enantio- and Diastereoselective Synthesis of Axially Chiral Compounds.Accounts of chemical research · 2022Article
- BINOL-Containing Chiral Porous Polymers as Platforms for Enantiorecognition.ACS applied materials & interfaces · 2022Article
- Organocatalytic cycloaddition of alkynylindoles with azonaphthalenes for atroposelective construction of indole-based biaryls.Nature communications · 2022Article
- Article
- Cu(i) catalysis for selective condensation/bicycloaromatization of two different arylalkynes: direct and general construction of functionalized C-N axial biaryl compounds.Chemical science · 2021Article
- Organocatalytic cycloaddition-elimination cascade for atroposelective construction of heterobiaryls.Chemical science · 2021Article
- Recent advances in the asymmetric phosphoric acid-catalyzed synthesis of axially chiral compounds.Beilstein journal of organic chemistry · 2021Review
- Enantioselective Iron/Bisquinolyldiamine Ligand-Catalyzed Oxidative Coupling Reaction of 2-Naphthols.Molecules (Basel, Switzerland) · 2020Article
- Bidirectional enantioselective synthesis of bis-benzofuran atropisomeric oligoarenes featuring two distal C-C stereogenic axes.Chemical science · 2020Article
- Article
- Organocatalytic atroposelective construction of axially chiral arylquinones.Nature communications · 2019Article
- Conversion of two stereocenters to one or two chiral axes: atroposelective synthesis of 2,3-diarylbenzoindoles.Chemical science · 2019Article
- Highly atroposelective synthesis of nonbiaryl naphthalene-1,2-diamine N-C atropisomers through direct enantioselective C-H amination.Nature communications · 2019Article
- NHC-catalyzed atropoenantioselective synthesis of axially chiral biaryl amino alcohols via a cooperative strategy.Nature communications · 2019Article
- Why do thioureas and squaramides slow down the Ireland-Claisen rearrangement?Beilstein journal of organic chemistry · 2019Article
- Enantioselective Vanadium-Catalyzed Oxidative Coupling: Development and Mechanistic Insights.The Journal of organic chemistry · 2018Article
- Enantioselective Synthesis of Biaryl Atropisomers via the Addition of Thiophenols into Aryl-Naphthoquinones.ACS catalysis · 2018Article
- Asymmetric Oxidative Coupling of Phenols and Hydroxycarbazoles.Organic letters · 2017Article
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6 authors.
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Abstract
Herein we disclose a scalable organocatalytic direct arylation approach for the regio- and atroposelective synthesis of non-C2-symmetric 2,2'-dihydroxy-1,1'-binaphthalenes (BINOLs). In the presence of catalytic amounts of axially chiral phosphoric acids, phenols and naphthols are coupled with iminoquinones via a cascade process that involves sequential aminal formation, sigmatropic rearrangement, and rearomatization to afford enantiomerically enriched BINOL derivatives in good to excellent yields. Our studies suggest that the (local) symmetry of the initially formed aminal intermediate has a dramatic impact on the level of enantioinduction in the final product. Aminals with a plane of symmetry give rise to BINOL derivatives with significantly lower enantiomeric excess than unsymmetrical ones featuring a stereogenic center. Presumably asymmetric induction in the sigmatropic rearrangement step is significantly more challenging than during aminal formation. Sigmatropic rearrangement of the enantiomerically enriched aminal and subsequent rearomatization transfers the central chirality into axial chirality with high fidelity.
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