ArticleNature chemistry2017
Catalytic enantioselective synthesis of atropisomeric biaryls by a cation-directed O-alkylation.
Article in Nature chemistry, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 35 papers.
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Who cites it
35 citing papers in PubMed, 235 citations in OpenAlex.
- Adamantyl-BOX Ligand Enabling Stereoselective Synthesis of Axially Chiral Aldehydes Bearing Vicinal Stereogenic Centers.ACS central science · 2026Article
- Organocatalytic asymmetric synthesis of atropisomeric tetraarylethenes: design, properties, and applications.Chemical science · 2026Article
- Alkyne Migratory Insertion Enabled Dynamic Kinetic Asymmetric Dearomatization of Unactivated Racemic Biaryls.Nature communications · 2026Article
- Recent Advances in Organocatalytic Kinetic Resolution for the Synthesis of Axially Chiral Compounds.Molecules (Basel, Switzerland) · 2026Review
- The Synthesis and Property Study of NH-Ac-Anchored Multilayer 3D Polymers.Molecules (Basel, Switzerland) · 2025Article
- Enantiopure Turbo Chirality Targets in Tri-Propeller Blades: Design, Asymmetric Synthesis, and Computational Analysis.Molecules (Basel, Switzerland) · 2025Article
- Stereoselective Synthesis of Axially Chiral Allenes and Styrenes via Chiral Phosphoric Acid Catalysis: An Overview.ACS omega · 2024Review
- Article
- Ni-catalysed assembly of axially chiral alkenes from alkynyl tetracoordinate borons via 1,3-metallate shift.Nature chemistry · 2024Article
- Catalytic Enantioselective Synthesis of Axially Chiral Imidazoles by Cation-Directed Desymmetrization.Journal of the American Chemical Society · 2023Article
- Axially chiral styrene-based organocatalysts and their application in asymmetric cascade Michael/cyclization reaction.Chemical science · 2023Article
- Interrogating the configurational stability of atropisomers.Nature protocols · 2023Review
- Rhodium-catalyzed atroposelective access to trisubstituted olefinsChemical science · 2023Article
- Counterion-Mediated Enantioconvergent Synthesis of Axially Chiral Medium Rings.Journal of the American Chemical Society · 2022Article
- Organocatalytic cycloaddition of alkynylindoles with azonaphthalenes for atroposelective construction of indole-based biaryls.Nature communications · 2022Article
- Carbene-catalyzed atroposelective synthesis of axially chiral styrenes.Nature communications · 2022Article
- 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
- Exploiting Configurational Lability in Aza-Sulfur Compounds for the Organocatalytic Enantioselective Synthesis of Sulfonimidamides.Angewandte Chemie (International ed. in English) · 2021Article
- Organocatalytic cycloaddition-elimination cascade for atroposelective construction of heterobiaryls.Chemical science · 2021Article
- Facile synthesis of axially chiral styrene-type carboxylic acidsChemical science · 2021Article
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Axially chiral biaryls, as exemplified by 1,1'-bi-2-naphthol (BINOL), are key components of catalysts, natural products and medicines. These materials are synthesized conventionally in enantioenriched form through metal-mediated cross coupling, de novo construction of an aromatic ring, point-to-axial chirality transfer or an atropselective transformation of an existing biaryl. Here, we report a highly enantioselective organocatalytic method for the synthesis of atropisomeric biaryls by a cation-directed O-alkylation. Treatment of racemic 1-aryl-2-tetralones with a chiral quinidine-derived ammonium salt under basic conditions in the presence of an alkylating agent leads to atropselective O-alkylation with e.r. up to 98:2. Oxidation with DDQ gives access to C
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.