Mostrar el registro sencillo del ítem
dc.contributor.author | Sierra, Sonia | es_ES |
dc.contributor.author | Gomez, M. Victoria | es_ES |
dc.contributor.author | Jimenez, Ana I. | es_ES |
dc.contributor.author | Pop, Alexandra | es_ES |
dc.contributor.author | Silvestru, Cristian | es_ES |
dc.contributor.author | Marín García, Mª Luisa | es_ES |
dc.contributor.author | Bosca Mayans, Francisco | es_ES |
dc.contributor.author | SASTRE NAVARRO, GERMAN IGNACIO | es_ES |
dc.contributor.author | Gomez-Bengoa, Enrique | es_ES |
dc.contributor.author | Urriolabeitia, Esteban P. | es_ES |
dc.date.accessioned | 2023-07-10T18:02:33Z | |
dc.date.available | 2023-07-10T18:02:33Z | |
dc.date.issued | 2022-03-04 | es_ES |
dc.identifier.issn | 0022-3263 | es_ES |
dc.identifier.uri | http://hdl.handle.net/10251/194777 | |
dc.description.abstract | [EN] The irradiation of (Z)-2-phenyl-4-aryliden-5(4H)-oxazolones 1 in deoxygenated CH2Cl2 at 25 degrees C with blue light (465 nm) in the presence of [Ru(bpy)(3)](BF4)(2) (5% mole ratio) as a triplet photocatalyst promotes the [2+2] photocycloaddition of the C=C bonds of the 4-arylidene moiety, thus allowing the completely regio- and stereoselective formation of cyclobutane-bis(oxazolone)s 2 as single stereoisomers. Cyclobutanes 2 have been unambiguously characterized as the mu-isomers and contain two E-oxazolones coupled in an anti-head-to-head form. The use of continuous-flow techniques in microreactors allows the synthesis of cyclobutanes 2 in only 60 min, compared with the 24-48 h required in batch mode. Ring opening of the oxazolone heterocycle in 2 with a base affords the corresponding 1,2-diaminotruxinic bis-amino esters 3, which are also obtained selectively as mu-isomers. The ruthenium complex behaves as a triplet photocatalyst, generating the reactive excited state of the oxazolone via an energy-transfer process. This reactive excited state has been characterized as a triplet diradical (3)(E/Z)-1* by laser flash photolysis (transient absorption spectroscopy). This technique also shows that this excited state is the same when starting from either (Z)- or (E)-oxazolones. Density functional theory calculations show that the first step of the [2+2] cycloaddition between (3)(E/Z)-1* and (Z)-1 is formation of the C(H)-C(H) bond and that (Z) to (E) isomerization takes place at the 1,4-diradical thus formed. | es_ES |
dc.description.sponsorship | The authors thank the Spanish Government for funding: Project PID2020-119636GB-I00, funded by MCIN/AEI/10.13039/501100011033; Projects PID2019-106394GB-I00/AEI/10.13039/501100011033, PID2019-110441RB-C33/AEI/10.13039/501100011033, and PID2019-110008GB-I00/AEI/10.13039/501100011033, funded by MCIN/AEI/10.13039/501100011033; Projects RTI2018-101784-B-I00, RTI2018-101033-B-I00, and CTQ2017-84825-R, funded by MCIN/AEI/10.13039/501100011033 and FEDER Una manera de hacer Europa. E.P.U., A.I.J., and S.S. thank Gobierno de Aragon-FSE (Spain, research group Aminoacidos y Peptidos E19_20R) for funding. G.S. thanks CTI-CSIC and ASIC-UPV for the use of computational facilities. E.G.-B. thanks SGIker (UPV/EHU) for providing human and computational resources. A.P. is grateful for the financial support of the Romanian Ministry of Education and Research through Grant PN-III-P1-1.1-MC-2018-2580. S.S. thanks Gobierno de Aragon-FSE for a Ph.D. fellowship. | es_ES |
dc.language | Inglés | es_ES |
dc.publisher | American Chemical Society | es_ES |
dc.relation.ispartof | Journal of Organic Chemistry | es_ES |
dc.rights | Reconocimiento (by) | es_ES |
dc.subject.classification | QUIMICA ORGANICA | es_ES |
dc.title | Stereoselective, Ruthenium-Photocatalyzed Synthesis of 1,2-Diaminotruxinic Bis-amino Acids from 4-Arylidene-5(4H)-oxazolones | es_ES |
dc.type | Artículo | es_ES |
dc.identifier.doi | 10.1021/acs.joc.1c03092 | es_ES |
dc.relation.projectID | info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2017-84825-R/ES/MICROBOBINAS DE RESONANCIA MAGNETICA NUCLEAR EN ESTUDIOS DE HIPERPOLARIZACION DE AMILOIDES/ | es_ES |
dc.relation.projectID | info:eu-repo/grantAgreement/UEFISCDI//PN-III-P1-1.1-MC-2018-2580/ | es_ES |
dc.relation.projectID | info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2019-106394GB-I00/ES/PROCESOS SOSTENIBLES PARA LA SINTESIS DE NUEVOS AMINOACIDOS, INCLUYENDO ESPECIES RELACIONADAS, Y SUS APLICACIONES/ | es_ES |
dc.relation.projectID | info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2019-110008GB-I00/ES/ESTUDIOS COMPUTACIONALES Y EXPERIMENTALES SOBRE ACTIVACION C-H CATALIZADA POR PALADIO/ | es_ES |
dc.relation.projectID | info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2019-110441RB-C33/ES/SINTESIS, CARACTERIZACION Y EVALUACION DE NUEVOS FOTOCATALIZADORES: ANALISIS DE PATOGENOS MICROBIANOS Y MICROCONTAMINANTES ORGANICOS COMO INDICADORES DE CALIDAD/ | es_ES |
dc.relation.projectID | info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2020-119636GB-I00/ES/DISEÑO, SINTESIS Y APLICACION DE GUIAS DE ONDA CON NUEVOS MATERIALES ORGANICOS/ | es_ES |
dc.relation.projectID | info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/RTI2018-101033-B-I00/ES/DISEÑO DE CATALIZADORES MULTIFUNCIONALES PARA LA CONVERSION EFICIENTE DE BIOGAS Y GAS NATURAL A HIDROCARBUROS DE INTERES INDUSTRIAL/ | es_ES |
dc.relation.projectID | info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/RTI2018-101784-B-I00/ES/NUEVOS MATERIALES ZEOLITICOS PARA PROCESOS DE SEPARACION SELECTIVA DE GASES, APLICACIONES MEDIOAMBIENTALES Y CONSERVACION DE ALIMENTOS/ | es_ES |
dc.rights.accessRights | Abierto | es_ES |
dc.contributor.affiliation | Universitat Politècnica de València. Escuela Técnica Superior de Ingenieros Industriales - Escola Tècnica Superior d'Enginyers Industrials | es_ES |
dc.description.bibliographicCitation | Sierra, S.; Gomez, MV.; Jimenez, AI.; Pop, A.; Silvestru, C.; Marín García, ML.; Bosca Mayans, F.... (2022). Stereoselective, Ruthenium-Photocatalyzed Synthesis of 1,2-Diaminotruxinic Bis-amino Acids from 4-Arylidene-5(4H)-oxazolones. Journal of Organic Chemistry. 87(5):3529-3545. https://doi.org/10.1021/acs.joc.1c03092 | es_ES |
dc.description.accrualMethod | S | es_ES |
dc.relation.publisherversion | https://doi.org/10.1021/acs.joc.1c03092 | es_ES |
dc.description.upvformatpinicio | 3529 | es_ES |
dc.description.upvformatpfin | 3545 | es_ES |
dc.type.version | info:eu-repo/semantics/publishedVersion | es_ES |
dc.description.volume | 87 | es_ES |
dc.description.issue | 5 | es_ES |
dc.identifier.pmid | 35143202 | es_ES |
dc.identifier.pmcid | PMC8902759 | es_ES |
dc.relation.pasarela | S\477823 | es_ES |
dc.contributor.funder | Gobierno de Aragón | es_ES |
dc.contributor.funder | AGENCIA ESTATAL DE INVESTIGACION | es_ES |
dc.contributor.funder | Agencia Estatal de Investigación | es_ES |
dc.contributor.funder | European Regional Development Fund | es_ES |
dc.contributor.funder | Executive Agency for Higher Education, Scientific Research, Development and Innovation Funding, Rumanía | es_ES |