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Synthetic scope and DFT analysis of the chiral binap-gold(I) complex-catalyzed 1,3-dipolar cycloaddition of azlactones with alkenes

dc.contributor.authorMartín Rodríguez, María
dc.contributor.authorCastelló, Luis M.
dc.contributor.authorNájera, Carmen
dc.contributor.authorSansano, José M.
dc.contributor.authorLarrañaga Agirre, Olatz
dc.contributor.authorDe Cózar Ruano, Abel
dc.contributor.authorCossío Mora, Fernando Pedro ORCID
dc.date.accessioned2014-02-04T18:11:40Z
dc.date.available2014-02-04T18:11:40Z
dc.date.issued2013-11
dc.identifier.citationBeilstein Journal of Organic Chemistry 9 : 2422–2433 (2013)es
dc.identifier.issn1860-5397
dc.identifier.urihttp://hdl.handle.net/10810/11341
dc.description.abstracthe 1,3-dipolar cycloaddition between glycine-derived azlactones with maleimides is efficiently catalyzed by the dimeric chiral complex [(S-a)-Binap.AuTFA](2). The alanine-derived oxazolone only reacts with tert-butyl acrylate giving anomalous regiochemistry, which is explained and supported by Natural Resonance Theory and Nucleus Independent Chemical Shifts calculations. The origin of the high enantiodiscrimination observed with maleimides and tert-butyl acrylate is analyzed using DFT computed at M06/Lanl2dz//ONIOM(b3lyp/Lanl2dz:UFF) level. Several applications of these cycloadducts in the synthesis of new proline derivatives with a 2,5-trans-arrangement and in the preparation of complex fused polycyclic molecules are described.es
dc.description.sponsorshipThis work has been supported by the DGES of the Spanish Ministerio de Ciencia e Innovacion (MICINN) (Consolider INGENIO 2010 CSD2007-00006, FEDER-CTQ2007-62771/BQU, CTQ2010-20387 and by the Hispano-Brazilian project PHB2008-0037-PC), Generalitat Valenciana (PROMETEO/2009/039), the Basque government (Grant IT-324-07) and by the University of Alicante. M. M.-R. and L. C. also thank DGES for grants. The authors also thank the SGI/IZO-SGIker of UPV/EHU for allocation of computational resources.es
dc.language.isoenges
dc.publisherBeilstein Institutes
dc.relationinfo:eu-repo/grantAgreement/MICINN/CSD2007-00006
dc.rightsinfo:eu-repo/semantics/openAccesses
dc.subjectasymmetric catalysises
dc.subjectDFTes
dc.subject1,3-dipolar cycloadditiones
dc.subjectgold catalysises
dc.subjectNICSes
dc.subjectNTRes
dc.subjectoxazoloneses
dc.subjectprolineses
dc.titleSynthetic scope and DFT analysis of the chiral binap-gold(I) complex-catalyzed 1,3-dipolar cycloaddition of azlactones with alkeneses
dc.typeinfo:eu-repo/semantics/articlees
dc.rights.holder© 2013 Martín-Rodríguez et al; licensee Beilstein-Institut. This is an Open Access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (http://www.beilstein-journals.org/bjoc)es
dc.relation.publisherversionhttp://www.beilstein-journals.org/bjoc/single/articleFullText.htm?publicId=1860-5397-9-280es
dc.identifier.doi10.3762/bjoc.9.280
dc.departamentoesQuímica orgánica Ies_ES
dc.departamentoeuKimika organikoa Ies_ES
dc.subject.categoriaCHEMISTRY, ORGANIC


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