ReviewNature protocols2023
Interrogating the configurational stability of atropisomers.
Review in Nature protocols, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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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.
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Who cites it
14 citing papers in PubMed, 45 citations in OpenAlex.
- The acylative kinetic resolution of 1,2-azaborine naphthols.Chemical science · 2026Article
- Copper-catalyzed enantioselective interrupted azide-alkyne cycloaddition to access axially chiral diaryl ethers.Chemical science · 2026Article
- Atroposelective Suzuki-Miyaura Coupling to Form 2-Amino-2'-Hydroxybiphenyls Enabled by sRuPhos.Angewandte Chemie (International ed. in English) · 2026Article
- Fluorescence mapping of atropisomer populations enabled by through-space conjugation.Nature communications · 2026Article
- Organocatalyzed atroposelective dynamic kinetic resolutions via transient seven-membered cyclic hemiacetals.Science advances · 2025Article
- Article
- Isothiourea-Catalysed Acylative Kinetic and Dynamic Kinetic Resolution of Planar Chiral Paracyclophanols.Angewandte Chemie (International ed. in English) · 2025Article
- Azapeptide Atropisomers From Late-StageThe Journal of organic chemistry · 2025Article
- All-Heteroatom-Substituted Carbon Spiro Stereocenters: Synthesis, Resolution, Enantiomeric Stability, and Absolute Configuration.Journal of the American Chemical Society · 2025Article
- Determination of the Enantiomerization Barrier of Midazolam in Aqueous Conditions by Electronic Circular Dichroism and Dynamic Enantioselective HPLC/UHPLC.Molecules (Basel, Switzerland) · 2025Article
- Metallo-azapeptides: Controlled Metal Chelation to Peptide Backbone Nitrogen.Journal of the American Chemical Society · 2025Article
- Investigating the diastereoselective synthesis of a macrocycle under Curtin-Hammett control.Chemical science · 2024Article
- A Chirally Locked Bis-perylene Diimide Macrocycle: Consequences for Chiral Self-Assembly and Circularly Polarized Luminescence.Journal of the American Chemical Society · 2024Article
- Studies on the Configurational Stability of Tropolone-Ketone-, Ester-, and Aldehyde-Based Chiral Axes.The Journal of organic chemistry · 2024Article
Corrections and comments
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Authors and funding
4 authors at 3 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Atropisomers are molecules whose stereogenicity arises from restricted rotation about a single bond. They are of current importance because of their applications in catalysis, medicine and materials science. The defining feature of atropisomeric molecules is that their stereoisomers are related to one another by bond rotation: as a result, evaluating their configurational stability (i.e., the rate at which their stereoisomers interconvert) is central to any work in this area. Important atropisomeric scaffolds include C-C linked biaryls, such as the ligand BINAP and the drug vancomycin, and C-N linked amine derivatives such as the drug telenzepine. This article focuses on the three most widely used experimental methods that are available to measure the rate of racemization in atropisomers, namely: (i) kinetic analysis of the racemization of an enantioenriched sample, (ii) dynamic HPLC and (iii) variable-temperature NMR. For each technique, an explanation of the theory is set out, followed by a detailed experimental procedure. A discussion is also included of which technique to try when confronted with a new molecular structure whose properties are not yet known. None of the three procedures require complex experimental techniques, and all can be performed by using standard analytical equipment (NMR and HPLC). The time taken to determine a racemization rate depends on which experimental method is required, but for a new compound it is generally possible to measure a racemization rate in <1 d.
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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.