Iron catalyzed highly enantioselective epoxidation of cyclic aliphatic enones with aqueous H2O2

An iron complex with a C1-symmetric tetradentate N-based ligand catalyzes the asymmetric epoxidation of cyclic enones and cyclohexene ketones with aqueous hydrogen peroxide, providing the corresponding epoxides in good to excellent yields and enantioselectivities (up to 99% yield, and 95% ee), under...

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Detalles Bibliográficos
Autores: Cussó Forest, Olaf, Cianfanelli, Marco, Ribas Salamaña, Xavi, Klein Gebbink, Robertus J M, Costas Salgueiro, Miquel
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2016
País:España
Institución:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
Repositorio:Recercat. Dipósit de la Recerca de Catalunya
OAI Identifier:oai:recercat.cat:10256/12121
Acceso en línea:http://hdl.handle.net/10256/12121
Access Level:acceso abierto
Palabra clave:Epòxids
Epoxy compounds
Catalitzadors
Catalysts
Ferro -- Oxidació
Iron -- Oxidation
Catàlisi asimètrica
Enantioselective catalysis
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spelling Iron catalyzed highly enantioselective epoxidation of cyclic aliphatic enones with aqueous H2O2Cussó Forest, OlafCianfanelli, MarcoRibas Salamaña, XaviKlein Gebbink, Robertus J MCostas Salgueiro, MiquelEpòxidsEpoxy compoundsCatalitzadorsCatalystsFerro -- OxidacióIron -- OxidationCatàlisi asimètricaEnantioselective catalysisAn iron complex with a C1-symmetric tetradentate N-based ligand catalyzes the asymmetric epoxidation of cyclic enones and cyclohexene ketones with aqueous hydrogen peroxide, providing the corresponding epoxides in good to excellent yields and enantioselectivities (up to 99% yield, and 95% ee), under mild conditions and in short reaction times. Evidence is provided that reactions involve an electrophilic oxidant, and this element is employed in performing site selective epoxidation of enones containing two alkene sitesWe acknowledge financial support from European Research Council (ERC‐2009‐StG‐239910), MINECO of Spain (CTQ2012‐37420‐C02‐01/BQU, Consolider‐Ingenio CSD2010‐00065) and the Catalan DIUE of the Generalitat de Catalunya (2009SGR637)American Chemical Society (ACS)Ministerio de Economía y Competitividad (Espanya)Ministerio de Ciencia e Innovación (Espanya)Generalitat de Catalunya. Agència de Gestió d'Ajuts Universitaris i de Recerca2016info:eu-repo/semantics/articleinfo:eu-repo/semantics/acceptedVersionapplication/pdfhttp://hdl.handle.net/10256/12121http://hdl.handle.net/10256/12121© Journal of the American Chemical Society, 2016, vol.138, núm. 8, p. 2732-2738Articles publicats (D-Q)reponame:Recercat. Dipósit de la Recerca de Catalunyainstname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)Inglésinfo:eu-repo/semantics/altIdentifier/doi/10.1021/jacs.5b12681info:eu-repo/semantics/altIdentifier/issn/0002-7863info:eu-repo/semantics/altIdentifier/eissn/1520-5126info:eu-repo/grantAgreement/MINECO//CTQ2012-37420-C02-01MICINN/PN 2010-2016/CSD2010-00065AGAUR/2009-2014/2009 SGR-637info:eu-repo/grantAgreement/EC/FP7/239910Tots els drets reservatsinfo:eu-repo/semantics/openAccessoai:recercat.cat:10256/121212026-05-29T05:05:01Z
dc.title.none.fl_str_mv Iron catalyzed highly enantioselective epoxidation of cyclic aliphatic enones with aqueous H2O2
title Iron catalyzed highly enantioselective epoxidation of cyclic aliphatic enones with aqueous H2O2
spellingShingle Iron catalyzed highly enantioselective epoxidation of cyclic aliphatic enones with aqueous H2O2
Cussó Forest, Olaf
Epòxids
Epoxy compounds
Catalitzadors
Catalysts
Ferro -- Oxidació
Iron -- Oxidation
Catàlisi asimètrica
Enantioselective catalysis
title_short Iron catalyzed highly enantioselective epoxidation of cyclic aliphatic enones with aqueous H2O2
title_full Iron catalyzed highly enantioselective epoxidation of cyclic aliphatic enones with aqueous H2O2
title_fullStr Iron catalyzed highly enantioselective epoxidation of cyclic aliphatic enones with aqueous H2O2
title_full_unstemmed Iron catalyzed highly enantioselective epoxidation of cyclic aliphatic enones with aqueous H2O2
title_sort Iron catalyzed highly enantioselective epoxidation of cyclic aliphatic enones with aqueous H2O2
dc.creator.none.fl_str_mv Cussó Forest, Olaf
Cianfanelli, Marco
Ribas Salamaña, Xavi
Klein Gebbink, Robertus J M
Costas Salgueiro, Miquel
author Cussó Forest, Olaf
author_facet Cussó Forest, Olaf
Cianfanelli, Marco
Ribas Salamaña, Xavi
Klein Gebbink, Robertus J M
Costas Salgueiro, Miquel
author_role author
author2 Cianfanelli, Marco
Ribas Salamaña, Xavi
Klein Gebbink, Robertus J M
Costas Salgueiro, Miquel
author2_role author
author
author
author
dc.contributor.none.fl_str_mv Ministerio de Economía y Competitividad (Espanya)
Ministerio de Ciencia e Innovación (Espanya)
Generalitat de Catalunya. Agència de Gestió d'Ajuts Universitaris i de Recerca
dc.subject.none.fl_str_mv Epòxids
Epoxy compounds
Catalitzadors
Catalysts
Ferro -- Oxidació
Iron -- Oxidation
Catàlisi asimètrica
Enantioselective catalysis
topic Epòxids
Epoxy compounds
Catalitzadors
Catalysts
Ferro -- Oxidació
Iron -- Oxidation
Catàlisi asimètrica
Enantioselective catalysis
description An iron complex with a C1-symmetric tetradentate N-based ligand catalyzes the asymmetric epoxidation of cyclic enones and cyclohexene ketones with aqueous hydrogen peroxide, providing the corresponding epoxides in good to excellent yields and enantioselectivities (up to 99% yield, and 95% ee), under mild conditions and in short reaction times. Evidence is provided that reactions involve an electrophilic oxidant, and this element is employed in performing site selective epoxidation of enones containing two alkene sites
publishDate 2016
dc.date.none.fl_str_mv 2016
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10256/12121
http://hdl.handle.net/10256/12121
url http://hdl.handle.net/10256/12121
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1021/jacs.5b12681
info:eu-repo/semantics/altIdentifier/issn/0002-7863
info:eu-repo/semantics/altIdentifier/eissn/1520-5126
info:eu-repo/grantAgreement/MINECO//CTQ2012-37420-C02-01
MICINN/PN 2010-2016/CSD2010-00065
AGAUR/2009-2014/2009 SGR-637
info:eu-repo/grantAgreement/EC/FP7/239910
dc.rights.none.fl_str_mv Tots els drets reservats
info:eu-repo/semantics/openAccess
rights_invalid_str_mv Tots els drets reservats
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv American Chemical Society (ACS)
publisher.none.fl_str_mv American Chemical Society (ACS)
dc.source.none.fl_str_mv © Journal of the American Chemical Society, 2016, vol.138, núm. 8, p. 2732-2738
Articles publicats (D-Q)
reponame:Recercat. Dipósit de la Recerca de Catalunya
instname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
instname_str Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
reponame_str Recercat. Dipósit de la Recerca de Catalunya
collection Recercat. Dipósit de la Recerca de Catalunya
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15.81155

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