MOF-808 as a Highly Active Catalyst for the Diastereoselective Reduction of Substituted Cyclohexanones
[EN] Zr-containing MOF-808 is an excellent heterogeneous catalyst for the diastereoselective Meerwein-Ponndorf-Verley reduction of substituted cyclohexanones. The presence of substituents at the 2 or 3 position of the cyclohexanone ring strongly drives the reaction towards the formation of one of th...
| Autores: | , |
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| Tipo de recurso: | artículo |
| Fecha de publicación: | 2022 |
| País: | España |
| Institución: | Universitat Politècnica de València (UPV) |
| Repositorio: | RiuNet. Repositorio Institucional de la Universitat Politécnica de Valéncia |
| Idioma: | inglés |
| OAI Identifier: | oai:riunet.upv.es:10251/193745 |
| Acceso en línea: | https://riunet.upv.es/handle/10251/193745 |
| Access Level: | acceso abierto |
| Palabra clave: | Zr metal-organic framework Meerwein-Ponndorf-Verley reaction Heterogeneous catalysis Substituted cyclohexanone 07.- Asegurar el acceso a energías asequibles, fiables, sostenibles y modernas para todos 08.- Fomentar el crecimiento económico sostenido, inclusivo y sostenible, el empleo pleno y productivo, y el trabajo decente para todos 09.- Desarrollar infraestructuras resilientes, promover la industrialización inclusiva y sostenible, y fomentar la innovación |
| Sumario: | [EN] Zr-containing MOF-808 is an excellent heterogeneous catalyst for the diastereoselective Meerwein-Ponndorf-Verley reduction of substituted cyclohexanones. The presence of substituents at the 2 or 3 position of the cyclohexanone ring strongly drives the reaction towards the formation of one of the two possible isomers. For 3-methyl cyclohexanone, the available space inside the MOF pores allows the formation of the bulkier transition state leading to the thermodynamically stable 3-cis-cyclohexanol. For 2-methyl cyclohexanone, the reaction rate is much slower and the final diastereoselectivity depends on the size of the alcohol used. Finally, reduction of 2-phenyl cyclohexanone is considerable faster over MOF-808 than for any other catalyst reported so far. The large size of the phenyl favors the selective formation (up to 94% selectivity) of the cis-alcohol, which goes through a less hindered transition state. |
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