ArticleThe Journal of organic chemistry2021
Mechanism of the Kinugasa Reaction Revisited.
Article in The Journal of organic chemistry, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.
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Who cites it
3 citing papers in PubMed.
- Nitrones: Comprehensive Review on Synthesis and Applications.Molecules (Basel, Switzerland) · 2025Review
- π-Bonding of Group 11 Metals to a Tantalum Alkylidyne Alkyl Complex Promotes Unusual Tautomerism to Bis-alkylidene and COJournal of the American Chemical Society · 2024Article
- Catalytic Enantioselective Alkyne Addition to Nitrones Enabled by Tunable Axially Chiral Imidazole-Based P,N-Ligands.Journal of the American Chemical Society · 2024Article
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Authors and funding
2 authors.
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Abstract
The mechanism of the Kinugasa reaction, that is, the copper-catalyzed formation of β-lactams from nitrones and terminal alkynes, is re-evaluated by means of density functional theory calculations and in light of recent experimental findings. Different possible mechanistic scenarios are investigated using phenanthroline as a ligand and triethylamine as a base. The calculations confirm that after an initial two-step cycloaddition promoted by two copper ions, the resulting five-membered ring intermediate can undergo a fast and irreversible cycloreversion to generate an imine and a dicopper-ketenyl intermediate. From there, the reaction can proceed through a nucleophilic attack of a ketenyl copper intermediate on the imine and an intramolecular cyclization, rather than through the previously suggested (2 + 2) Staudinger synthesis.
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