ArticleChemical science2019
Conversion of two stereocenters to one or two chiral axes: atroposelective synthesis of 2,3-diarylbenzoindoles.
Article in Chemical science, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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16 citing papers in PubMed.
- Article
- Human Endothelial Membrane as a Structural Prototype: A Comparative Analysis withInternational journal of molecular sciences · 2026Article
- Divergent Synthesis of Chiroptical Molecular Switches Based on 1,2-Diaxial Atropisomers.JACS Au · 2024Article
- Copper-catalysed asymmetric annulation of yne-allylic esters with amines to access axially chiral arylpyrroles.Nature communications · 2024Article
- Chiral dinitrogen ligand enabled asymmetric Pd/norbornene cooperative catalysis toward the assembly of C-N axially chiral scaffolds.Nature communications · 2024Article
- Catalytic Asymmetric Diastereodivergent Synthesis of 2-Alkenylindoles Bearing both Axial and Central Chirality.Precision chemistry · 2024Article
- Asymmetric Synthesis of Axially Chiral Molecules via Organocatalytic Cycloaddition and Cyclization Reactions.Molecules (Basel, Switzerland) · 2023Review
- Enantioselective Synthesis of Atropisomers by Oxidative Aromatization with Central-to-Axial Conversion of Chirality.Molecules (Basel, Switzerland) · 2023Review
- Enantioselective construction of triaryl-substituted all-carbon quaternary stereocentersChemical science · 2023Article
- Design and synthesis of axially chiral aryl-pyrroloindoles via the strategy of organocatalytic asymmetric (2 + 3) cyclization.Fundamental research · 2023Article
- Advances in the Asymmetric Synthesis of BINOL Derivatives.Molecules (Basel, Switzerland) · 2022Review
- Organocatalytic cycloaddition of alkynylindoles with azonaphthalenes for atroposelective construction of indole-based biaryls.Nature communications · 2022Article
- 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
- Catalytic Dynamic Kinetic Resolutions in Tandem to Construct Two-Axis Terphenyl Atropisomers.Journal of the American Chemical Society · 2020Article
- Bidirectional enantioselective synthesis of bis-benzofuran atropisomeric oligoarenes featuring two distal C-C stereogenic axes.Chemical science · 2020Article
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7 authors.
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Abstract
Central-to-axial chirality conversion provides efficient access to axially chiral compounds, and several examples regarding the conversion of one, two or four stereocenters to one axis have been reported. Herein, we report the conversion of two stereocenters to one or two chiral axes for the first time. In this study, a new class of enantiomerically enriched 2,3-diarylbenzoindoles was efficiently synthesized using a chiral phosphoric acid-catalyzed [3 + 2] formal cycloaddition and a mild DDQ oxidation strategy. Moreover, a speculative model of the central-to-axial chirality conversion outcome was proposed based on preliminary mechanistic studies and DFT calculations. Potentially, using this strategy, useful chiral phosphine ligand can be synthesized smoothly (99% ee).
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