ArticleThe Journal of organic chemistry2023
Lewis Acid-Catalyzed Carbonyl-Ene Reaction: Interplay between Aromaticity, Synchronicity, and Pauli Repulsion.
Article in The Journal of organic chemistry, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed, 17 citations in OpenAlex.
- Zr-Site Lewis Acidity Determines Terpenoid Reduction Selectivity.ACS catalysis · 2026Article
- Unveiling the Role of the Lewis Acids in the Acceleration of Alder-Ene Reactions: A Molecular Electron Density Theory Study.Molecules (Basel, Switzerland) · 2025Article
- Exploring CORSC advances · 2025Article
- Influence of the Nature of Group 15 Element on [AuInorganic chemistry · 2025Article
- Transition-state aromaticity and its relationship with reactivity in pericyclic reactions.Beilstein journal of organic chemistry · 2025Article
- Facile and Highly Selective Deprotection of Aryl Propionates/Acetates Using a Supported Lewis Acid Catalyst (20% InClACS omega · 2024Article
- Domino dehydration/intermolecular (enantioselective) ketone-ene reactions catalysed by a simple solid in batch and in flow.RSC advances · 2024Article
- Origin of the Felkin-Anh(-Eisenstein) model: a quantitative rationalization of a seminal concept.Chemical science · 2024Article
- Mechanistic Insights into the DABCO-Catalyzed Cloke-Wilson Rearrangement: A DFT Perspective.The Journal of organic chemistry · 2023Article
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Authors and funding
4 authors at 2 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The physical factors governing the catalysis in Lewis acid-promoted carbonyl-ene reactions have been explored in detail quantum chemically. It is found that the binding of a Lewis acid to the carbonyl group directly involved in the transformation greatly accelerates the reaction by decreasing the corresponding activation barrier up to 25 kcal/mol. The Lewis acid makes the process much more asynchronous and the corresponding transition state less in-plane aromatic. The remarkable acceleration induced by the catalyst is ascribed, by means of the activation strain model and the energy decomposition analysis methods, mainly to a significant reduction of the Pauli repulsion between the key occupied π-molecular orbitals of the reactants and not to the widely accepted stabilization of the LUMO of the enophile.
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Registered trials
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