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Enantioselective Synthesis of 5-Trifluoromethyl-2-oxazolines under Dual Silver/Organocatalysis

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Enantioselective Synthesis of 5-Trifluoromethyl-2-oxazolines under Dual Silver/Organocatalysis

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dc.contributor.author Martinez-Pardo, Pablo es_ES
dc.contributor.author Blay, Gonzalo es_ES
dc.contributor.author Vila, Carlos es_ES
dc.contributor.author Sanz-Marco, Amparo es_ES
dc.contributor.author Muñoz Roca, María Del Carmen es_ES
dc.contributor.author Pedro, Jose R. es_ES
dc.date.accessioned 2020-07-10T03:31:32Z
dc.date.available 2020-07-10T03:31:32Z
dc.date.issued 2019 es_ES
dc.identifier.issn 0022-3263 es_ES
dc.identifier.uri http://hdl.handle.net/10251/147736
dc.description.abstract [EN] The first enantioselective formal [3 + 2] cycloaddition between ¿-isocyanoesters and trifluoromethylketones to give 5-trifluoromethyl-2-oxazolines bearing two contiguous stereogenic centers, one of them being a quaternary stereocenter substituted with a CF3 group, has been developed. The reaction is based upon a multicatalytic approach that combines a bifunctional Brønsted base-squaramide organocatalyst and Ag+ as Lewis acid. The reaction could be achieved with a range of aryl and heteroaryl trifluoromethyl ketones, and the resulting oxazolines were obtained with good to excellent diastereo- and enantioselectivity. es_ES
dc.description.sponsorship Financial support from the MINECO and FEDER (CTQ2017-84900-P). Access to NMR and MS facilities from SCSIE-UV. C.V. thanks the Spanish Government for a Ramon y Cajal contract (RyC-2016-20187). A.S.-M. thanks the Generalitat Valenciana and Fondo Social Europeo for a postdoctoral grant (APOST/2016/139). es_ES
dc.language Inglés es_ES
dc.publisher American Chemical Society es_ES
dc.relation.ispartof The Journal of Organic Chemistry es_ES
dc.rights Reserva de todos los derechos es_ES
dc.subject.classification FISICA APLICADA es_ES
dc.title Enantioselective Synthesis of 5-Trifluoromethyl-2-oxazolines under Dual Silver/Organocatalysis es_ES
dc.type Artículo es_ES
dc.identifier.doi 10.1021/acs.joc.8b02808 es_ES
dc.relation.projectID info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2017-84900-P/ES/REACCIONES DE ADICION ENANTIOSELECTIVAS MEDIANTE SISTEMAS MULTICATALITICOS. HERRAMIENTAS PARA LA SINTESIS EFICIENTE DE MOLECULAS CON ACTIVIDAD FARMACOLOGICA/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/MINECO//RYC-2016-20187/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/GVA//APOSTD%2F2016%2F139/ es_ES
dc.rights.accessRights Abierto es_ES
dc.contributor.affiliation Universitat Politècnica de València. Departamento de Física Aplicada - Departament de Física Aplicada es_ES
dc.description.bibliographicCitation Martinez-Pardo, P.; Blay, G.; Vila, C.; Sanz-Marco, A.; Muñoz Roca, MDC.; Pedro, JR. (2019). Enantioselective Synthesis of 5-Trifluoromethyl-2-oxazolines under Dual Silver/Organocatalysis. The Journal of Organic Chemistry. 84(1):314-325. https://doi.org/10.1021/acs.joc.8b02808 es_ES
dc.description.accrualMethod S es_ES
dc.relation.publisherversion https://doi.org/10.1021/acs.joc.8b02808 es_ES
dc.description.upvformatpinicio 314 es_ES
dc.description.upvformatpfin 325 es_ES
dc.type.version info:eu-repo/semantics/publishedVersion es_ES
dc.description.volume 84 es_ES
dc.description.issue 1 es_ES
dc.identifier.pmid 30537821 es_ES
dc.identifier.pmcid 04-01-2019 es_ES
dc.relation.pasarela S\392181 es_ES
dc.contributor.funder European Social Fund es_ES
dc.contributor.funder Generalitat Valenciana es_ES
dc.contributor.funder European Regional Development Fund es_ES
dc.contributor.funder Agencia Estatal de Investigación es_ES
dc.contributor.funder Ministerio de Economía y Competitividad es_ES


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