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dc.contributor.author | Padín Santos, Damián |
dc.contributor.author | Cambeiro Cambeiro, Fermín |
dc.contributor.author | Fañanás Mastral, Martín |
dc.contributor.author | Varela Carrete, Jesús Ángel |
dc.contributor.author | Saá Rodríguez, Carlos |
dc.date.accessioned | 2020-10-05T07:00:32Z |
dc.date.available | 2020-10-05T07:00:32Z |
dc.date.issued | 2016 |
dc.identifier.citation | 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 |
dc.identifier.uri | http://hdl.handle.net/10347/23353 |
dc.description | NOTICE: 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.abstract | Aza-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.sponsorship | This 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.iso | eng |
dc.publisher | American Chemical Society |
dc.rights | Copyright © 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.subject | Carbenes |
dc.subject | [2+1] Cycloaddition |
dc.subject | Diazo compounds |
dc.subject | Pyrrolidines |
dc.subject | Ruthenium catalyst |
dc.title | [2+1] Cycloaddition of Catalytic Ruthenium Vinyl Carbenes: A Stereoselective Controlled Access to (Z)- and (E)-Vinyl Epoxypyrrolidines |
dc.type | journal article |
dc.identifier.doi | 10.1021/acscatal.6b02929 |
dc.relation.publisherversion | https://doi.org/10.1021/acscatal.6b02929 |
dc.type.hasVersion | AM |
dc.identifier.essn | 2155-5435 |
dc.rights.accessRights | open access |
dc.contributor.affiliation | Universidade de Santiago de Compostela. Centro de Investigación en Química Biolóxica e Materiais Moleculares |
dc.contributor.affiliation | Universidade de Santiago de Compostela. Departamento de Química Orgánica |
dc.description.peerreviewed | SI |
dc.relation.projectID | info: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.projectID | info: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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