ArticleJournal of the American Chemical Society2015
Enantioselective synthesis of 3-arylquinazolin-4(3H)-ones via peptide-catalyzed atroposelective bromination.
Article in Journal of the American Chemical Society, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 52 papers.
What it found
Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.
The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.
Who cites it
52 citing papers in PubMed.
- Access to C─N and N─N Axially Chiral Pyridinones via NHC-Catalyzed Dynamic Kinetic Resolution of Rotationally Restricted Cyclic Imides.Angewandte Chemie (International ed. in English) · 2026Article
- Copper-Catalyzed Asymmetric Hydroboration of Alkynes to C-N Axially Chiral Azaborines via Dynamic Kinetic Resolution.Angewandte Chemie (International ed. in English) · 2026Article
- Chiral phosphoric acid-catalyzed atroposelective iodination of N-arylindoles.Communications chemistry · 2025Article
- Identifying and Engineering Flavin Dependent Halogenases for Selective Biocatalysis.Accounts of chemical research · 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
- 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
- β-Turn Induction by a Diastereopure Azepane-Derived Quaternary Amino Acid.The Journal of organic chemistry · 2023Article
- Asymmetric catalysis by flavin-dependent halogenases.Chirality · 2023Review
- Atropisomerism in the Pharmaceutically Relevant Realm.Accounts of chemical research · 2022Article
- Article
- Article
- Construction of Non-Biaryl Atropisomeric Amide Scaffolds Bearing a C-N Axis via Enantioselective Catalysis.Molecules (Basel, Switzerland) · 2022Review
- Directed Evolution of Flavin-Dependent Halogenases for Site- and Atroposelective Halogenation of 3-Aryl-4(3Journal of the American Chemical Society · 2022Article
- Asymmetric Synthesis of Axially Chiral C-N Atropisomers.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Review
- Thioether-enabled palladium-catalyzed atroposelective C-H olefination for N-C and C-C axial chirality.Chemical science · 2022Article
- Catalytic atroposelective dynamic kinetic resolutions and kinetic resolutions towards 3-arylquinolinesChemical communications (Cambridge, England) · 2021Article
- Stapled β-Hairpins Featuring 4-Mercaptoproline.Journal of the American Chemical Society · 2021Article
- Atroposelective synthesis ofChemical science · 2021Article
- Enantioselective Aromatic Amination?Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
4 authors.
Funding
Abstract
We report the development of a tertiary amine-containing β-turn peptide that catalyzes the atroposelective bromination of pharmaceutically relevant 3-arylquinazolin-4(3H)-ones (quinazolinones) with high levels of enantioinduction over a broad substrate scope. The structure of the free catalyst and the peptide-substrate complex were explored using X-ray crystallography and 2D-NOESY experiments. Quinazolinone rotational barriers about the chiral anilide axis were also studied using density functional theory calculations and are discussed in light of the high enantioselectivities observed. Mechanistic studies also suggest that the initial bromination event is stereodetermining, and the major monobromide intermediate is an atropisomerically stable, mono-ortho-substituted isomer. The observation of stereoisomerically stable monobromides stimulated the conversion of the tribromide products to other atropisomerically defined products of interest. For example, (1) a dehalogenation Suzuki-Miyaura cross-coupling sequence delivers ortho-arylated derivatives, and (2) a regioselective Buchwald-Hartwig amination procedure installs para-amine functionality. Stereochemical information was retained during these subsequent transformations.
Indexed as
Identifiers
What OpenQuestion holds
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.