ArticleACS catalysis2018
Enantioselective Synthesis of Biaryl Atropisomers via the Addition of Thiophenols into Aryl-Naphthoquinones.
Article in ACS catalysis, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed.
- Violet-light-induced ring expansion of 2-aryl-1,3-indandiones with chlorodiazirines toward 1,4-naphthoquinones.Chemical science · 2026Article
- Bifunctional Squaramide-Catalyzed Oxidative Kinetic Resolution: Simultaneous Access to Axially Chiral Thioether and Sulfoxide.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Dynamic Kinetic Resolution of Indole-Based Sulfenylated Heterobiaryls by Rhodium-Catalyzed Atroposelective Reductive Aldol Reaction.ACS catalysis · 2023Article
- Catalytic Atroposelective Synthesis ofJournal of the American Chemical Society · 2020Article
- Bidirectional enantioselective synthesis of bis-benzofuran atropisomeric oligoarenes featuring two distal C-C stereogenic axes.Chemical science · 2020Article
- Recent Progress in the Development of Fluorescent Probes for Thiophenol.Molecules (Basel, Switzerland) · 2019Review
- Article
- Towards a Catalytic Atroposelective Synthesis of Diaryl Ethers via C(Synlett : accounts and rapid communications in synthetic organic chemistry · 2018Article
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7 authors.
Funding
Abstract
We report a cinchona alkaloid catalyzed addition of thiophenol into rapidly interconverting aryl-naphthoquinones, resulting in stable biaryl atropisomers upon reductive methylation. An array of thiophenols and naphthoquinone substrates were evaluated, and we observed selectivities up to 98.5:1.5 e.r. Control of the quinone redox properties allowed us to study the stereochemical stabilities of each oxidation state of the substrates. The resulting enantioenriched products can also be moved on via an S
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