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dc.contributor.author | Mautschke, H.-H. | es_ES |
dc.contributor.author | Llabrés i Xamena, Francesc Xavier | es_ES |
dc.date.accessioned | 2022-07-14T18:04:08Z | |
dc.date.available | 2022-07-14T18:04:08Z | |
dc.date.issued | 2021-07-21 | es_ES |
dc.identifier.issn | 0947-6539 | es_ES |
dc.identifier.uri | http://hdl.handle.net/10251/184208 | |
dc.description.abstract | [EN] Zr-containing MOF-808 is a very promising heterogeneous catalyst for the selective reduction of ketosteroids to the corresponding hydroxysteroids through a Meerwein-Ponndorf-Verley (MPV) reaction. Interestingly, the process leads to the diastereoselective synthesis of elusive 17 alpha-hydroxy derivatives in one step, whereas most chemical and biological transformations produce the 17 beta-OH compounds, or they require several additional steps to convert 17 beta-OH into 17 alpha-OH by inverting the configuration of the 17 center. Moreover, MOF-808 is found to be stable and reusable; it is also chemoselective (only keto groups are reduced, even in the presence of other reducible groups such as C=C bonds) and regioselective (in 3,17-diketosteroids only the keto group in position 17 is reduced, while the 3-keto group remains almost intact). The kinetic rate constant and thermodynamic parameters of estrone reduction to estradiol have been obtained by a detailed temperature-dependent kinetic analysis. The results evidence a major contribution of the entropic term, thus suggesting that the diastereoselectivity of the process is controlled by the confinement of the reaction inside the MOF cavities, where the Zr4+ active sites are located. | es_ES |
dc.description.sponsorship | Financial support by the Spanish Government is acknowledged through projects MAT2017-82288-C2-1-P and the Severo Ochoa program (SEV-2016-0683). The Microscopy Service of the Universitat Politecnica de Valencia is gratefully acknowledged for the electron microscopy images. | es_ES |
dc.language | Inglés | es_ES |
dc.publisher | John Wiley & Sons | es_ES |
dc.relation.ispartof | Chemistry - A European Journal | es_ES |
dc.rights | Reconocimiento (by) | es_ES |
dc.subject | Heterogeneous catalysis | es_ES |
dc.subject | Meerwein-Ponndorf-Verley | es_ES |
dc.subject | Metal-organic frameworks | es_ES |
dc.subject | Steroids | es_ES |
dc.title | One-Step Chemo-, Regio- and Stereoselective Reduction of Ketosteroids to Hydroxysteroids over Zr-Containing MOF-808 Metal-Organic Frameworks | es_ES |
dc.type | Artículo | es_ES |
dc.identifier.doi | 10.1002/chem.202100967 | es_ES |
dc.relation.projectID | info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/MAT2017-82288-C2-1-P/ES/MATERIALES HIBRIDOS MULTIFUNCIONALES BASADOS EN NANO-UNIDADES ESTRUCTURALES ACTIVAS/ | es_ES |
dc.relation.projectID | info:eu-repo/grantAgreement/MINECO//SEV-2016-0683//Programa Estatal de Fomento de la Investigación Científica y Técnica de Excelencia/ | es_ES |
dc.rights.accessRights | Abierto | es_ES |
dc.contributor.affiliation | Universitat Politècnica de València. Instituto Universitario Mixto de Tecnología Química - Institut Universitari Mixt de Tecnologia Química | es_ES |
dc.description.bibliographicCitation | Mautschke, H.; Llabrés I Xamena, FX. (2021). One-Step Chemo-, Regio- and Stereoselective Reduction of Ketosteroids to Hydroxysteroids over Zr-Containing MOF-808 Metal-Organic Frameworks. Chemistry - A European Journal. 27(41):10766-10775. https://doi.org/10.1002/chem.202100967 | es_ES |
dc.description.accrualMethod | S | es_ES |
dc.relation.publisherversion | https://doi.org/10.1002/chem.202100967 | es_ES |
dc.description.upvformatpinicio | 10766 | es_ES |
dc.description.upvformatpfin | 10775 | es_ES |
dc.type.version | info:eu-repo/semantics/publishedVersion | es_ES |
dc.description.volume | 27 | es_ES |
dc.description.issue | 41 | es_ES |
dc.identifier.pmid | 33998732 | es_ES |
dc.identifier.pmcid | PMC8362071 | es_ES |
dc.relation.pasarela | S\453571 | es_ES |
dc.contributor.funder | Ministerio de Economía y Competitividad | es_ES |
dc.contributor.funder | Ministerio Ciencia, Innovación y Universidades | es_ES |