Synthesis of esters of diaminotruxillic bis-amino acids by Pd-mediated photocycloaddition of analogs of the Kaede protein chromophore

Urriolabeitia, E.P. (Universidad de Zaragoza) ; Sanchez, P. ; Pop, A. ; Silvestru, C. ; Laga, E. ; Jimenez, A.I. (Universidad de Zaragoza) ; Cativiela, C. (Universidad de Zaragoza)

Resumen: The 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.

Idioma: Inglés

DOI: 10.3762/bjoc.16.98

Año: 2020

Publicado en: BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY 16 (2020), 1111-1123
ISSN: 1860-5397

Factor impacto JCR: 2.883 (2020)

Categ. JCR: CHEMISTRY, ORGANIC rank: 23 / 57 = 0.404 (2020) - Q2 - T2

Factor impacto SCIMAGO: 0.765 - Organic Chemistry (Q2)

Financiación: info:eu-repo/grantAgreement/ES/DGA/E19-20R
Financiación: info:eu-repo/grantAgreement/ES/DGA-FEDER/Construyendo Europa desde Aragón
Financiación: info:eu-repo/grantAgreement/ES/DGA-FEDER/LMP144-18

Tipo y forma: Artículo (Versión definitiva)

Área (Departamento): Área Química Inorgánica (Dpto. Química Inorgánica)
Área (Departamento): Área Química Orgánica (Dpto. Química Orgánica)