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dc.contributor.authorPadín Santos, Damián
dc.contributor.authorCambeiro Cambeiro, Fermín
dc.contributor.authorFañanás Mastral, Martín
dc.contributor.authorVarela Carrete, Jesús Ángel
dc.contributor.authorSaá Rodríguez, Carlos
dc.date.accessioned2020-10-05T07:00:32Z
dc.date.available2020-10-05T07:00:32Z
dc.date.issued2016
dc.identifier.citationPadín, D., Cambeiro, F., Fañanás-Mastral, M., Varela, J. A., Saá, C. (2017). [2+1] Cycloaddition of Catalytic Ruthenium Vinyl Carbenes: A Stereoselective Controlled Access to (Z)- and (E)-Vinyl Epoxypyrrolidines. ACS Catalysis, 7, 2, 992-996
dc.identifier.urihttp://hdl.handle.net/10347/23353
dc.descriptionNOTICE: This is the peer reviewed version of the following article: Padín, D., Cambeiro, F., Fañanás-Mastral, M., Varela, J. A., Saá, C. (2017). [2+1] Cycloaddition of Catalytic Ruthenium Vinyl Carbenes: A Stereoselective Controlled Access to (Z)- and (E)-Vinyl Epoxypyrrolidines. ACS Catalysis, 7, 2, 992-996. [doi: 10.1021/acscatal.6b02929]. This article may be used for non-commercial purposes in accordance with American Chemical Society Terms and Conditions for self-archiving
dc.description.abstractAza-alkynals undergo a cyclization reaction with diazo compounds in the presence of catalytic amounts of Cp*RuCl(cod) to afford vinyl epoxypyrrolidines, valuable building blocks for the synthesis of biologically active molecules. Ruthenium vinyl carbene intermediates have been invoked to explain the overall [2 + 1] cycloaddition (epoxy-annulation reaction). The reaction proceeds under mild conditions and in short reaction times (5–80 min) with complete (Z)- or (E)-stereoselectivity on the vinyl substituent, depending on the nature of the diazo compound used. Theoretical calculations support a mechanistic rationale to explain this controlled process.
dc.description.sponsorshipThis work was supported by the Spanish MINECO (project CTQ2014-59015R), the ERDF and the Xunta de Galicia (project GRC2014/032). We also thank the ORFEO-CINQA network (CTQ2014-51912REDC). D. P. thanks MEC for a predoctoral FPU fellowship (FPU15/02132). M. F.-M. thanks MINECO for a “Ramón y Cajal” contract
dc.language.isoeng
dc.publisherAmerican Chemical Society
dc.rightsCopyright © 2016 American Chemical Society. This article may be used for non-commercial purposes in accordance with American Chemical Society Terms and Conditions for self-archiving
dc.subjectCarbenes
dc.subject[2+1] Cycloaddition
dc.subjectDiazo compounds
dc.subjectPyrrolidines
dc.subjectRuthenium catalyst
dc.title[2+1] Cycloaddition of Catalytic Ruthenium Vinyl Carbenes: A Stereoselective Controlled Access to (Z)- and (E)-Vinyl Epoxypyrrolidines
dc.typejournal article
dc.identifier.doi10.1021/acscatal.6b02929
dc.relation.publisherversionhttps://doi.org/10.1021/acscatal.6b02929
dc.type.hasVersionAM
dc.identifier.essn2155-5435
dc.rights.accessRightsopen access
dc.contributor.affiliationUniversidade de Santiago de Compostela. Centro de Investigación en Química Biolóxica e Materiais Moleculares
dc.contributor.affiliationUniversidade de Santiago de Compostela. Departamento de Química Orgánica
dc.description.peerreviewedSI
dc.relation.projectIDinfo:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2014-59015R/ES/SINTESIS SOSTENIBLE DE FARMACOFOROS HETEROCICLICOS Y GRAFENOS BIFENILENICOS MEDIANTE TRANSFORMACIONES CATALITICAS ORGANOMETALICAS
dc.relation.projectIDinfo:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2014-51912/ES/RED ORFEO-CINQA "CENTRO DE INNOVACION EN QUIMICA AVANZADA”


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