ArticleAdvanced science (Weinheim, Baden-Wurttemberg, Germany)2024
Catalytic Enantioselective Synthesis of Axially Chiral Diaryl Ethers Via Asymmetric Povarov Reaction Enabled Desymmetrization.
Article in Advanced science (Weinheim, Baden-Wurttemberg, Germany), 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed.
- Enantioselective Synthesis of Axially Chiral Diaryl Ethers via Rhodium-Catalyzed [2 + 2 + 2] Cycloaddition.Angewandte Chemie (International ed. in English) · 2026Article
- Copper-catalyzed enantioselective interrupted azide-alkyne cycloaddition to access axially chiral diaryl ethers.Chemical science · 2026Article
- Enantiotopic-group-selective coupling for unified access to carbazole atropisomers as versatile chiral chromophores.Nature communications · 2025Article
- Chiral phosphoric acid-catalyzed asymmetric synthesis of helically chiral, planarly chiral and inherently chiral molecules.Beilstein journal of organic chemistry · 2025Review
- Measuring the stereogenic remoteness in non-central chirality: a stereocontrol connectivity index for asymmetric reactions.Beilstein journal of organic chemistry · 2025Article
- Atroposelective synthesis of axially chiral imidazo[1,2-Science advances · 2024Article
- Catalytic Enantioselective Synthesis of Axially Chiral Diaryl Ethers Via Asymmetric Povarov Reaction Enabled Desymmetrization.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
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5 authors.
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Abstract
Axially chiral diaryl ethers represent a distinct class of atropisomers, characterized by a unique dual C─O axes system, which have been found in a variety of natural products, pharmaceuticals, and ligands. However, the catalytic enantioselective synthesis of these atropoisomers poses significant challenges, due to the difficulty in controlling both chiral C─O axes, and their more flexible conformations. Herein, an efficient protocol for catalytic enantioselective synthesis of axially chiral diaryl ethers is presented using organocatalyzed asymmetric Povarov reaction-enabled desymmetrization, followed by aromatizations. This method yields a wide range of novel quinoline-based diaryl ether atropoisomers in good yields and high enantioselectivities. Notably, various aromatization protocols are developed, resulting in a diverse set of polysubstituted quinoline-containing diaryl ether atropisomers. Thermal racemization studies suggested excellent configurational stabilities for these novel diaryl ether atropisomers (with racemization barriers up to 38.1 kcal mol
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