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

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...

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Main Authors:	Esteban P. Urriolabeitia, Pablo Sánchez, Alexandra Pop, Cristian Silvestru, Eduardo Laga, Ana I. Jiménez, Carlos Cativiela
Format:	Article
Language:	English
Published:	Beilstein-Institut 2020-05-01
Series:	Beilstein Journal of Organic Chemistry
Subjects:	amino acids c–h activation kaede protein oxazolones photocycloaddition
Online Access:	https://doi.org/10.3762/bjoc.16.98

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spelling	doaj-fee42e17edf94f3799c87cf965ce4dcd2021-04-02T11:33:03ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972020-05-011611111112310.3762/bjoc.16.981860-5397-16-98Synthesis of esters of diaminotruxillic bis-amino acids by Pd-mediated photocycloaddition of analogs of the Kaede protein chromophoreEsteban P. Urriolabeitia0Pablo Sánchez1Alexandra Pop2Cristian Silvestru3Eduardo Laga4Ana I. Jiménez5Carlos Cativiela6Instituto de Síntesis Química y Catálisis Homogénea, ISQCH (CSIC - Universidad de Zaragoza), Pedro Cerbuna 12, E-50009 Zaragoza, SpainInstituto de Síntesis Química y Catálisis Homogénea, ISQCH (CSIC - Universidad de Zaragoza), Pedro Cerbuna 12, E-50009 Zaragoza, SpainSupramolecular Organic and Organometallic Chemistry Centre, Departament of Chemistry, Faculty of Chemistry and Chemical Engineering, Babeş-Bolyai University, Str. Arany Janos 11, RO-400028 Cluj−Napoca, RomaniaSupramolecular Organic and Organometallic Chemistry Centre, Departament of Chemistry, Faculty of Chemistry and Chemical Engineering, Babeş-Bolyai University, Str. Arany Janos 11, RO-400028 Cluj−Napoca, RomaniaInstituto de Síntesis Química y Catálisis Homogénea, ISQCH (CSIC - Universidad de Zaragoza), Pedro Cerbuna 12, E-50009 Zaragoza, SpainInstituto de Síntesis Química y Catálisis Homogénea, ISQCH (CSIC - Universidad de Zaragoza), Pedro Cerbuna 12, E-50009 Zaragoza, SpainInstituto de Síntesis Química y Catálisis Homogénea, ISQCH (CSIC - Universidad de Zaragoza), Pedro Cerbuna 12, E-50009 Zaragoza, SpainThe 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.https://doi.org/10.3762/bjoc.16.98amino acidsc–h activationkaede proteinoxazolonesphotocycloaddition
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Esteban P. Urriolabeitia Pablo Sánchez Alexandra Pop Cristian Silvestru Eduardo Laga Ana I. Jiménez Carlos Cativiela
spellingShingle	Esteban P. Urriolabeitia Pablo Sánchez Alexandra Pop Cristian Silvestru Eduardo Laga Ana I. Jiménez Carlos Cativiela Synthesis of esters of diaminotruxillic bis-amino acids by Pd-mediated photocycloaddition of analogs of the Kaede protein chromophore Beilstein Journal of Organic Chemistry amino acids c–h activation kaede protein oxazolones photocycloaddition
author_facet	Esteban P. Urriolabeitia Pablo Sánchez Alexandra Pop Cristian Silvestru Eduardo Laga Ana I. Jiménez Carlos Cativiela
author_sort	Esteban P. Urriolabeitia
title	Synthesis of esters of diaminotruxillic bis-amino acids by Pd-mediated photocycloaddition of analogs of the Kaede protein chromophore
title_short	Synthesis of esters of diaminotruxillic bis-amino acids by Pd-mediated photocycloaddition of analogs of the Kaede protein chromophore
title_full	Synthesis of esters of diaminotruxillic bis-amino acids by Pd-mediated photocycloaddition of analogs of the Kaede protein chromophore
title_fullStr	Synthesis of esters of diaminotruxillic bis-amino acids by Pd-mediated photocycloaddition of analogs of the Kaede protein chromophore
title_full_unstemmed	Synthesis of esters of diaminotruxillic bis-amino acids by Pd-mediated photocycloaddition of analogs of the Kaede protein chromophore
title_sort	synthesis of esters of diaminotruxillic bis-amino acids by pd-mediated photocycloaddition of analogs of the kaede protein chromophore
publisher	Beilstein-Institut
series	Beilstein Journal of Organic Chemistry
issn	1860-5397
publishDate	2020-05-01
description	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.
topic	amino acids c–h activation kaede protein oxazolones photocycloaddition
url	https://doi.org/10.3762/bjoc.16.98
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Synthesis of esters of diaminotruxillic bis-amino acids by Pd-mediated photocycloaddition of analogs of the Kaede protein chromophore

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