MOF-808 as a Highly Active Catalyst for the Diastereoselective Reduction of Substituted Cyclohexanones

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...

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Detalhes bibliográficos
Autores: Mautschke, Hans-Hilmar, Llabrés i Xamena, Francesc X.
Formato: artículo
Estado:Versión publicada
Fecha de publicación:2022
País:España
Recursos:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/296141
Acesso em linha:http://hdl.handle.net/10261/296141
Access Level:acceso abierto
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spelling MOF-808 as a Highly Active Catalyst for the Diastereoselective Reduction of Substituted CyclohexanonesMautschke, Hans-HilmarLlabrés i Xamena, Francesc X.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.Grant PID2020-112590GB-C21 funded by MCIN/AEI/ 10.13039/501100011033.Molecular Diversity Preservation InternationalMinisterio de Ciencia e Innovación (España)Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]2023202320222023info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Publisher's versioninfo:eu-repo/semantics/publishedVersionhttp://hdl.handle.net/10261/296141reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Inglés#PLACEHOLDER_PARENT_METADATA_VALUE#info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2020-112590GB-C21http://dx.doi.org/10.3390/molecules27196315Síinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/2961412026-05-22T06:33:51Z
dc.title.none.fl_str_mv MOF-808 as a Highly Active Catalyst for the Diastereoselective Reduction of Substituted Cyclohexanones
title MOF-808 as a Highly Active Catalyst for the Diastereoselective Reduction of Substituted Cyclohexanones
spellingShingle MOF-808 as a Highly Active Catalyst for the Diastereoselective Reduction of Substituted Cyclohexanones
Mautschke, Hans-Hilmar
title_short MOF-808 as a Highly Active Catalyst for the Diastereoselective Reduction of Substituted Cyclohexanones
title_full MOF-808 as a Highly Active Catalyst for the Diastereoselective Reduction of Substituted Cyclohexanones
title_fullStr MOF-808 as a Highly Active Catalyst for the Diastereoselective Reduction of Substituted Cyclohexanones
title_full_unstemmed MOF-808 as a Highly Active Catalyst for the Diastereoselective Reduction of Substituted Cyclohexanones
title_sort MOF-808 as a Highly Active Catalyst for the Diastereoselective Reduction of Substituted Cyclohexanones
dc.creator.none.fl_str_mv Mautschke, Hans-Hilmar
Llabrés i Xamena, Francesc X.
author Mautschke, Hans-Hilmar
author_facet Mautschke, Hans-Hilmar
Llabrés i Xamena, Francesc X.
author_role author
author2 Llabrés i Xamena, Francesc X.
author2_role author
dc.contributor.none.fl_str_mv Ministerio de Ciencia e Innovación (España)
Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
description 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.
publishDate 2022
dc.date.none.fl_str_mv 2022
2023
2023
2023
dc.type.none.fl_str_mv info:eu-repo/semantics/article
http://purl.org/coar/resource_type/c_6501
Publisher's version
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10261/296141
url http://hdl.handle.net/10261/296141
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv #PLACEHOLDER_PARENT_METADATA_VALUE#
info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2020-112590GB-C21
http://dx.doi.org/10.3390/molecules27196315
Sí
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Molecular Diversity Preservation International
publisher.none.fl_str_mv Molecular Diversity Preservation International
dc.source.none.fl_str_mv reponame:DIGITAL.CSIC. Repositorio Institucional del CSIC
instname:Consejo Superior de Investigaciones Científicas (CSIC)
instname_str Consejo Superior de Investigaciones Científicas (CSIC)
reponame_str DIGITAL.CSIC. Repositorio Institucional del CSIC
collection DIGITAL.CSIC. Repositorio Institucional del CSIC
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,811543

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