000089903 001__ 89903
000089903 005__ 20210902121818.0
000089903 0247_ $$2doi$$a10.3762/bjoc.16.98
000089903 0248_ $$2sideral$$a118303
000089903 037__ $$aART-2020-118303
000089903 041__ $$aeng
000089903 100__ $$0(orcid)0000-0001-9779-5820$$aUrriolabeitia, E.P.$$uUniversidad de Zaragoza
000089903 245__ $$aSynthesis of esters of diaminotruxillic bis-amino acids by Pd-mediated photocycloaddition of analogs of the Kaede protein chromophore
000089903 260__ $$c2020
000089903 5060_ $$aAccess copy available to the general public$$fUnrestricted
000089903 5203_ $$aThe stereoselective synthesis of truxillic bis-amino esters from polyfunctional oxazolones is reported. The reaction of 4-((Z)-arylidene)-2-(E)-styryl-5(4H)-oxazolones 2 with Pd(OAc)(2) resulted in ortho-palladation and the formation of a dinuclear open-book complexes 3 with carboxylate bridges, where the Pd atom is C<^>N bonded to the oxazolone. In 3 the two exocyclic C=C bonds of the oxazolone are in a face-to-face arrangement, which is optimal for their [2 + 2] photocycloaddition. Irradiation of dimers 3 in CH2Cl2 solution with blue light (465 nm) promoted the chemo- and stereoselective [2 + 2] photocycloaddition of the exocyclic C=C bonds and the formation of cyclobutane-containing ortho-palladated complexes 4. Treatment of 4 with CO in a MeOH/NCMe mixture promoted the methoxycarbonylation of the palladated carbon and the release of the corresponding ortho-functionalized 1, 3-diaminotruxillic bis-amino esters 5 as single isomers.
000089903 536__ $$9info:eu-repo/grantAgreement/ES/DGA/E19-20R$$9info:eu-repo/grantAgreement/ES/DGA-FEDER/Construyendo Europa desde Aragón$$9info:eu-repo/grantAgreement/ES/DGA-FEDER/LMP144-18
000089903 540__ $$9info:eu-repo/semantics/openAccess$$aby$$uhttp://creativecommons.org/licenses/by/3.0/es/
000089903 590__ $$a2.883$$b2020
000089903 591__ $$aCHEMISTRY, ORGANIC$$b23 / 57 = 0.404$$c2020$$dQ2$$eT2
000089903 592__ $$a0.765$$b2020
000089903 593__ $$aOrganic Chemistry$$c2020$$dQ2
000089903 655_4 $$ainfo:eu-repo/semantics/article$$vinfo:eu-repo/semantics/publishedVersion
000089903 700__ $$aSanchez, P.
000089903 700__ $$aPop, A.
000089903 700__ $$aSilvestru, C.
000089903 700__ $$0(orcid)0000-0003-1882-2558$$aLaga, E.
000089903 700__ $$0(orcid)0000-0001-8057-4861$$aJimenez, A.I.$$uUniversidad de Zaragoza
000089903 700__ $$0(orcid)0000-0003-3222-0828$$aCativiela, C.$$uUniversidad de Zaragoza
000089903 7102_ $$12010$$2760$$aUniversidad de Zaragoza$$bDpto. Química Inorgánica$$cÁrea Química Inorgánica
000089903 7102_ $$12013$$2765$$aUniversidad de Zaragoza$$bDpto. Química Orgánica$$cÁrea Química Orgánica
000089903 773__ $$g16 (2020), 1111-1123$$pBeilstein J. Org. Chem.$$tBEILSTEIN JOURNAL OF ORGANIC CHEMISTRY$$x1860-5397
000089903 8564_ $$s428139$$uhttps://zaguan.unizar.es/record/89903/files/texto_completo.pdf$$yVersión publicada
000089903 8564_ $$s347752$$uhttps://zaguan.unizar.es/record/89903/files/texto_completo.jpg?subformat=icon$$xicon$$yVersión publicada
000089903 909CO $$ooai:zaguan.unizar.es:89903$$particulos$$pdriver
000089903 951__ $$a2021-09-02-10:06:22
000089903 980__ $$aARTICLE