ArticleNature communications2022
Brønsted acid-enhanced copper-catalyzed atroposelective cycloisomerization to axially chiral arylquinolizones via dearomatization of pyridine.
Article in Nature communications, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed.
- Enantioselective Pd-Catalyzed Electrochemical Dearomative Allylation of Tropones: Construction of All-C Quaternary Stereocenters.Organic letters · 2026Article
- Synthesis of Quinolizidine-Based 1,4-Azaphosphinines via Cyclization of Heteroarylmethyl(alkynyl)phosphinates.The Journal of organic chemistry · 2026Article
- Reaction strategies for the meta-selective functionalization of pyridine through dearomatization.Molecular diversity · 2025Review
- Recent Strategies in the Nucleophilic Dearomatization of Pyridines, Quinolines, and Isoquinolines.Chemical reviews · 2024Review
- Recent Progresses in the Catalytic Stereoselective Dearomatization of Pyridines.Molecules (Basel, Switzerland) · 2023Review
- Advances in Atroposelectively De Novo Synthesis of Axially Chiral Heterobiaryl Scaffolds.Molecules (Basel, Switzerland) · 2022Review
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Authors and funding
4 authors.
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Abstract
The construction of axially chiral N-heterobiaryls is of great interest as a result of their occurrence in organocatalysts, chiral ligands, natural products, and biologically active molecules. Despite remarkable achievements in this area, strategies for the preparation of new classes of axially chiral N-heterobiaryls remain to be further explored. Herein, we report the enantioselective synthesis of axially chiral arylquinolizones through an intramolecular atroposelective cycloisomerization. The reaction proceeds via the Brønsted acid-enhanced dearomatization of pyridine by a copper catalyst that allows for the formation of the desired products in excellent yields and enantioselectivities. The utility of this methodology is illustrated by a synthesis on gram scale production and transformation of the products into chiral thiourea catalysts. Mechanistic studies demonstrate that Brønsted acid plays a significant role in promoting the reactivity of the reaction, while both the steric and electronic effects of aryl substituents in substrate play a role in controlling the stereoselectivity.
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