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Chiral gold(I) vs chiral silver complexes as catalysts for the enantioselective synthesis of the second generation GSK-hepatitis C virus inhibitor

dc.contributor.authorMartín Rodríguez, María
dc.contributor.authorNájera, Carmen
dc.contributor.authorSansano, José M.
dc.contributor.authorDe Cózar Ruano, Abel
dc.contributor.authorCossío Mora, Fernando Pedro ORCID
dc.date.accessioned2014-02-20T17:30:26Z
dc.date.available2014-02-20T17:30:26Z
dc.date.issued2011-07
dc.identifier.citationBeilstein Journal of Organic Chemistry 7 : 988–996 (2011)es
dc.identifier.issn1860-5397
dc.identifier.urihttp://hdl.handle.net/10810/11592
dc.description.abstractThe synthesis of a GSK 2(nd) generation inhibitor of the hepatitis C virus, by enantioselective 1,3-dipolar cycloaddition between a leucine derived iminoester and tert-butyl acrylate, was studied. The comparison between silver(I) and gold(I) catalysts in this reaction was established by working with chiral phosphoramidites or with chiral BINAP. The best reaction conditions were used for the total synthesis of the hepatitis C virus inhibitor by a four step procedure affording this product in 99% ee and in 63% overall yield. The origin of the enantioselectivity of the chiral gold(I) catalyst was justified according to DFT calculations, the stabilizing coulombic interaction between the nitrogen atom of the thiazole moiety and one of the gold atoms being crucial.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, CTQ2007/67528, 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. Also thanks DGES for a grant.es
dc.language.isoenges
dc.publisherBeilstein Institutes
dc.relationinfo:eu-repo/grantAgreement/MICINN/CSD2007-00006
dc.rightsinfo:eu-repo/semantics/openAccesses
dc.subjectBINAPes
dc.subject1,3-dipolar cycloadditiones
dc.subjectgoldes
dc.subjectHCVes
dc.subjectphosphoramiditees
dc.subjectsilveres
dc.subjectviral inhibitores
dc.titleChiral gold(I) vs chiral silver complexes as catalysts for the enantioselective synthesis of the second generation GSK-hepatitis C virus inhibitores
dc.typeinfo:eu-repo/semantics/articlees
dc.rights.holder© 2011 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=1860-5397-7-111es
dc.identifier.doi10.3762/bjoc.7.111
dc.departamentoesQuímica orgánica Ies_ES
dc.departamentoeuKimika organikoa Ies_ES
dc.subject.categoriaCHEMISTRY, ORGANIC


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