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Título: | Lewis Acid-Catalyzed Carbonyl-Ene Reaction: Interplay between Aromaticity, Synchronicity, and Pauli Repulsion |
Autor: | Rodríguez, Humberto A. CSIC ORCID; Cruz, Daniel A. CSIC ORCID; Padrón, Juan I. CSIC ORCID ; Fernández, Israel | Palabras clave: | Addition reactions carbonyls chemical reactions Lewis acids transfer reactions |
Fecha de publicación: | 24-jul-2023 | Editor: | ACS Publications | Citación: | The Journal of Organic Chemistry 88, 15: 11102–11110 (2023) | Resumen: | 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. | Versión del editor: | https://doi.org/10.1021/acs.joc.3c01059 | URI: | http://hdl.handle.net/10261/334735 | DOI: | 10.1021/acs.joc.3c01059 | ISSN: | 0022-3263 | E-ISSN: | 1520-6904 |
Aparece en las colecciones: | (IPNA) Artículos |
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Lewis-Rodriguez_et_al-2023-JOC.pdf | Artículo principal | 3,58 MB | Adobe PDF | Visualizar/Abrir |
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