ArticleJournal of the American Chemical Society2020
Catalytic Dynamic Kinetic Resolutions in Tandem to Construct Two-Axis Terphenyl Atropisomers.
Article in Journal of the American Chemical Society, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 21 papers.
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Who cites it
21 citing papers in PubMed.
- Alkyne Migratory Insertion Enabled Dynamic Kinetic Asymmetric Dearomatization of Unactivated Racemic Biaryls.Nature communications · 2026Article
- Article
- Recent advances in the stereoselective synthesis of distal biaxially chiral molecules.Beilstein journal of organic chemistry · 2026Review
- Asymmetric synthesis of chiral boronic esters featuring nonadjacent axial and flexible, acyclic central chirality.Science advances · 2025Article
- Peptide-Catalyzed Asymmetric Amination of Sulfenamides Enabled by DFT-Guided Catalyst Optimization.Journal of the American Chemical Society · 2025Article
- Organocatalyzed atroposelective dynamic kinetic resolutions via transient seven-membered cyclic hemiacetals.Science advances · 2025Article
- Recent advances in organocatalytic atroposelective reactions.Beilstein journal of organic chemistry · 2025Review
- Copper-catalysed asymmetric annulation of yne-allylic esters with amines to access axially chiral arylpyrroles.Nature communications · 2024Article
- Atroposelective catalysis.Nature reviews. Chemistry · 2024Review
- Chiral dinitrogen ligand enabled asymmetric Pd/norbornene cooperative catalysis toward the assembly of C-N axially chiral scaffolds.Nature communications · 2024Article
- Atroposelective synthesis of biaxial bridged eight-membered terphenyls via a Co/SPDO-catalyzed aerobic oxidative coupling/desymmetrization of phenols.Nature communications · 2024Article
- Scaffold-Oriented Asymmetric Catalysis: Conformational Modulation of Transition State Multivalency during a Catalyst-Controlled Assembly of a Pharmaceutically Relevant Atropisomer.Chemistry (Weinheim an der Bergstrasse, Germany) · 2024Article
- Diastereodivergent Catalysis.JACS Au · 2023Review
- Catalytic atroposelective synthesis of heterobiaryls with vicinal C-C and N-N diaxes via dynamic kinetic resolution.iScience · 2023Article
- Axially chiral styrene-based organocatalysts and their application in asymmetric cascade Michael/cyclization reaction.Chemical science · 2023Article
- Rhodium-catalyzed enantioselective and diastereodivergent access to diaxially chiral heterocycles.Nature communications · 2023Article
- Construction of C-B axial chirality via dynamic kinetic asymmetric cross-coupling mediated by tetracoordinate boron.Nature communications · 2023Article
- A Dynamic Thermodynamic Resolution Strategy for the Stereocontrolled Synthesis of Streptonigrin.Angewandte Chemie (International ed. in English) · 2023Article
- Synthesis of Atropisomeric Two-Axis Systems by the Catalyst-Controlled syn- and anti-Selective Arene-Forming Aldol Condensation.Angewandte Chemie (International ed. in English) · 2022Article
- Atroposelective Desymmetrization of Resorcinol-Bearing Quinazolinones via Cu-Catalyzed C-O Bond Formation.Organic letters · 2022Article
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4 authors.
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Abstract
The defined structure of molecules bearing multiple stereogenic axes is of increasing relevance to materials science, pharmaceuticals, and catalysis. However, catalytic enantioselective approaches to control multiple stereogenic axes remain synthetically challenging. We report the catalytic synthesis of two-axis terphenyl atropisomers, with complementary strategies to both chlorinated and brominated variants, formed with high diastereo- and enantioselectivity. The chemistry proceeds through a sequence of two distinct dynamic kinetic resolutions: first, an atroposelective ring opening of Bringmann-type lactones produces a product with one established axis of chirality, and second, a stereoselective arene halogenation delivers the product with the second axis of chirality established. In order to achieve these results, a class of Brønsted basic guanidinylated peptides, which catalyze an efficient atroposelective chlorination, is reported for the first time. In addition, a complementary bromination is reported, which also establishes the second stereogenic axis. These bromo-terphenyls are accessible following the discovery that chiral anion phase transfer catalysis by
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