DFT Studies on the Stereoselective Three-Component Ugi Reaction
studied theoretically based on DFT calculations. Structures of reagents, products, intermediates, and transition states were optimized at M062X/6-31+g(d,p) level of theory in gas phase and in methanol as a common solvent for this reaction. The reaction takes place through several processes, includin...
| Autores: | , |
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| Tipo de recurso: | artículo |
| Estado: | Versión publicada |
| Fecha de publicación: | 2019 |
| País: | Brasil |
| Institución: | Universidade Federal de Mato Grosso do Sul (UFMS) |
| Repositorio: | Orbital - The Electronic Journal of Chemistry (Campo Grande) |
| Idioma: | inglés |
| OAI Identifier: | oai:periodicos.ufms.br:article/16004 |
| Acceso en línea: | https://periodicos.ufms.br/index.php/orbital/article/view/16004 |
| Access Level: | acceso abierto |
| Palabra clave: | DFT calculation multicomponent reaction stereoselectivity three-component Ugi reaction |
| Sumario: | studied theoretically based on DFT calculations. Structures of reagents, products, intermediates, and transition states were optimized at M062X/6-31+g(d,p) level of theory in gas phase and in methanol as a common solvent for this reaction. The reaction takes place through several processes, including atom inversion, bond rotation, acid-base, nucleophile-electrophile competitions. These diverse phenomena were studied to provide a clearer picture of the mechanism of this valuable reaction, especially in terms of stereochemistry considerations. According to the results, the enthalpy of the reaction was -45.9 and -41.2 kcal/mol for the dominant product in gas phase and in methanol. The stereoselectivity of the reaction was under the kinetic control of nucleophilic attack of isocyanide to less hindered si-face (Ea= 4.1 compared to 7.4 kcal/mol for re-face) of more stable chiral (E)-iminium in methanol. DOI: http://dx.doi.org/10.17807/orbital.v11i1.1214 |
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