ArticleOrganic letters2019
Troponoid Atropisomerism: Studies on the Configurational Stability of Tropone-Amide Chiral Axes.
Article in Organic letters, 2019. 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.
- Synthetic, Computational, and Experimental Studies of a Class 3 Atropisomeric α-Naphthyl Tropone.The Journal of organic chemistry · 2025Article
- Deconstruction of Desacetamidocolchicine's B Ring Reveals a Class 3 Atropisomeric AC Ring with Tubulin Binding Properties.The Journal of organic chemistry · 2025Article
- Studies on the Configurational Stability of Tropolone-Ketone-, Ester-, and Aldehyde-Based Chiral Axes.The Journal of organic chemistry · 2024Article
- Interrogating the configurational stability of atropisomers.Nature protocols · 2023Review
- Carbocycloaddition Strategies for Troponoid Synthesis.Tetrahedron · 2023Article
- Atropisomerism in the Pharmaceutically Relevant Realm.Accounts of chemical research · 2022Article
- Asymmetric Catalysis Mediated by Synthetic Peptides, Version 2.0: Expansion of Scope and Mechanisms.Chemical reviews · 2020Review
- Amide-containing α-hydroxytropolones as inhibitors of hepatitis B virus replication.Antiviral research · 2020Article
Corrections and comments
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Authors and funding
6 authors.
Funding
Abstract
Configurationally stable, atropisomeric motifs are an important structural element in a number of molecules, including chiral ligands, catalysts, and molecular devices. Thus, understanding features that stabilize chiral axes is of fundamental interest throughout the chemical sciences. The following details the high rotational barriers about the Ar-C(O) bond of tropone amides, which significantly exceed those of analogous benzamides. These studies are supported by both experimental and computational rotational barrier measurements. We also report the resolution of an axially chiral α-hydroxytropolone amide into its individual atropisomers, and demonstrate its configurational stability at physiological pH and temperatures over 24 h.
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