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Título: | Theoretical (DFT) insights into the mechanism of copper-catalyzed cyclopropanation reactions. Implications for enantioselective catalysis |
Autor: | Fraile, José M. CSIC ORCID ; García, José I. CSIC ORCID ; Martínez-Merino, Víctor; Mayoral, José A. CSIC ORCID; Salvatella, Luis CSIC ORCID | Fecha de publicación: | 2001 | Editor: | American Chemical Society | Citación: | Journal of the American Chemical Society 123(31): 7616-7625 (2001) | Resumen: | The mechanism of the copper(I)-catalyzed cyclopropanation reaction has been extensively investigated for a medium-size reaction model by means of B3LYP/6-31G(d) calculations. The starting ethylene complex of the N,N‘-dimethylmalonaldiimine−copper (I) catalyst undergoes a ligand exchange with methyl diazoacetate to yield a reaction intermediate, which subsequently undergoes nitrogen extrusion to generate a copper−carbene complex. The cyclopropanation step takes place through a direct carbene insertion of the metal−carbene species to yield a catalyst−product complex, which can finally regenerate the starting complex. The stereochemical predictions of a more realistic model (by considering a chiral bis(oxazoline)−copper (I) catalyst) have been rationalized in terms of steric repulsions, showing good agreement with experimental data. | Versión del editor: | https://doi.org/10.1021/ja003695c | URI: | http://hdl.handle.net/10261/272879 | DOI: | 10.1021/ja003695c | ISSN: | 0002-7863 |
Aparece en las colecciones: | (ICMA) Artículos |
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