dc.contributor.author | Martín Rodríguez, María | |
dc.contributor.author | Castelló, Luis M. | |
dc.contributor.author | Nájera, Carmen | |
dc.contributor.author | Sansano, José M. | |
dc.contributor.author | Larrañaga Agirre, Olatz | |
dc.contributor.author | De Cózar Ruano, Abel | |
dc.contributor.author | Cossío Mora, Fernando Pedro ![ORCID](/themes/Mirage2//images/orcid_16x16.png) | |
dc.date.accessioned | 2014-02-04T18:11:40Z | |
dc.date.available | 2014-02-04T18:11:40Z | |
dc.date.issued | 2013-11 | |
dc.identifier.citation | Beilstein Journal of Organic Chemistry 9 : 2422–2433 (2013) | es |
dc.identifier.issn | 1860-5397 | |
dc.identifier.uri | http://hdl.handle.net/10810/11341 | |
dc.description.abstract | he 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.sponsorship | This 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.iso | eng | es |
dc.publisher | Beilstein Institut | es |
dc.relation | info:eu-repo/grantAgreement/MICINN/CSD2007-00006 | |
dc.rights | info:eu-repo/semantics/openAccess | es |
dc.subject | asymmetric catalysis | es |
dc.subject | DFT | es |
dc.subject | 1,3-dipolar cycloaddition | es |
dc.subject | gold catalysis | es |
dc.subject | NICS | es |
dc.subject | NTR | es |
dc.subject | oxazolones | es |
dc.subject | prolines | es |
dc.title | Synthetic scope and DFT analysis of the chiral binap-gold(I) complex-catalyzed 1,3-dipolar cycloaddition of azlactones with alkenes | es |
dc.type | info:eu-repo/semantics/article | es |
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.publisherversion | http://www.beilstein-journals.org/bjoc/single/articleFullText.htm?publicId=1860-5397-9-280 | es |
dc.identifier.doi | 10.3762/bjoc.9.280 | |
dc.departamentoes | Química orgánica I | es_ES |
dc.departamentoeu | Kimika organikoa I | es_ES |
dc.subject.categoria | CHEMISTRY, ORGANIC | |