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Regio-, Diastereo-, and Enantioselective Organocatalytic Addition of 4-Substituted Pyrazolones to Isatin-Dereved Nitroalkenes

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Regio-, Diastereo-, and Enantioselective Organocatalytic Addition of 4-Substituted Pyrazolones to Isatin-Dereved Nitroalkenes

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dc.contributor.author Vila, C. es_ES
dc.contributor.author Dharmaraj, N. R. es_ES
dc.contributor.author Faubel, A. es_ES
dc.contributor.author Blay, G. es_ES
dc.contributor.author Cardona, M. L. es_ES
dc.contributor.author Muñoz Roca, María Del Carmen es_ES
dc.contributor.author Pedro, J. R. es_ES
dc.date.accessioned 2020-03-23T08:46:06Z
dc.date.available 2020-03-23T08:46:06Z
dc.date.issued 2019-05-26 es_ES
dc.identifier.issn 1434-193X es_ES
dc.identifier.uri http://hdl.handle.net/10251/139151
dc.description This is the peer reviewed version of the following article: [FULL CITE], which has been published in final form at [Link to final article using the DOI]. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving. es_ES
dc.description.abstract [EN] Hydroquinine 2,5-diphenyl-4,6-pyrimidinediyl diether [(DHQ)(2)Pyr] catalyzed the regio-, diastereo-, and enantioselective addition of 4-substituted pyrazolones to isatin-derived nitroalkenes, providing a variety of chiral alkenylpyrazolone adducts containing a tetrasubstituted stereocenter bearing an oxindole moiety with excellent yields, regioselectivity, and diastereoselectivity, as well as a moderate enantioselectivity (up to 98 % yield, > 20:1 E/Z ratio dr and 78 % ee). The reaction harnesses a nitroalkene as an alkenylating agent through a Nucleophilic Vinylic Substitution (SNV) reaction. es_ES
dc.description.sponsorship Financial support from the Agencia Estatal de Investigacion (AEI, Spanish Government) and Fondo Europeo de Desarrollo Regional (FEDER, European Union) (CTQ2017-84900-P) is acknowledged. C. V. thanks the Spanish Government for Ramon y Cajal contract (RYC-2016-20187). Access to NMR, MS, and Xray facilities of the Servei Central de Suport a la Investigacio Experimental (SCSIE)-UV is also acknowledged. es_ES
dc.language Inglés es_ES
dc.publisher John Wiley & Sons es_ES
dc.relation.ispartof European Journal of Organic Chemistry es_ES
dc.rights Reserva de todos los derechos es_ES
dc.subject Asymmetric catalysis es_ES
dc.subject Nitroalkenes es_ES
dc.subject Pyrazolones es_ES
dc.subject Organocatalysis es_ES
dc.subject Nucleophilic substitution es_ES
dc.subject.classification FISICA APLICADA es_ES
dc.title Regio-, Diastereo-, and Enantioselective Organocatalytic Addition of 4-Substituted Pyrazolones to Isatin-Dereved Nitroalkenes es_ES
dc.type Artículo es_ES
dc.identifier.doi 10.1002/ejoc.201900328 es_ES
dc.relation.projectID info:eu-repo/grantAgreement/MINECO//RYC-2016-20187/ 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.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 Vila, C.; Dharmaraj, NR.; Faubel, A.; Blay, G.; Cardona, ML.; Muñoz Roca, MDC.; Pedro, JR. (2019). Regio-, Diastereo-, and Enantioselective Organocatalytic Addition of 4-Substituted Pyrazolones to Isatin-Dereved Nitroalkenes. European Journal of Organic Chemistry. (19):3040-3044. https://doi.org/10.1002/ejoc.201900328 es_ES
dc.description.accrualMethod S es_ES
dc.relation.publisherversion https://doi.org/10.1002/ejoc.201900328 es_ES
dc.description.upvformatpinicio 3040 es_ES
dc.description.upvformatpfin 3044 es_ES
dc.type.version info:eu-repo/semantics/publishedVersion es_ES
dc.description.issue 19 es_ES
dc.relation.pasarela S\392182 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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