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dc.contributor.authorSanjuán Cortázar, Ana María 
dc.contributor.authorRashid, Muhammad A. 
dc.contributor.authorGarcía García, Patricia
dc.contributor.authorMartínez Cuezva, Alberto 
dc.contributor.authorFernández Rodríguez, Manuel A. 
dc.contributor.authorRodríguez, Félix
dc.contributor.authorSanz Díez, Roberto 
dc.date.accessioned2015-12-10T12:48:00Z
dc.date.available2016-02-09T03:45:06Z
dc.date.issued2015-02
dc.identifier.issn0947-6539
dc.identifier.urihttp://hdl.handle.net/10259/3895
dc.description.abstractIndenes and related polycyclic structures have been efficiently synthesized by gold(I)-catalyzed cycloisomerizations of appropriate ortho-(alkynyl)styrenes. Disubstitution at the terminal position of the olefin was demonstrated to be essential to obtain products originating from a formal 5-endo-dig cyclization. Interestingly, a complete switch in the selectivity of the cyclization of o-(alkynyl)-α-methylstyrenes from 6-endo to 5-endo was observed by adding an alcohol to the reaction media. This allowed the synthesis of interesting indenes bearing an all-carbon quaternary center at C1. Moreover, dihydrobenzo[a]fluorenes can be obtained from substrates bearing a secondary alkyl group at the β-position of the styrene moiety by a tandem cycloisomerization/1,2-hydride migration process. In addition, diverse polycyclic compounds were obtained by an intramolecular gold-catalyzed alkoxycyclization of o-(alkynyl)styrenes bearing a nucleophile in their structure. Finally, the use of a chiral gold complex allowed access to elusive chiral 1H-indenes in good enantioselectivitiesen
dc.description.sponsorshipMinisterio de Economia y Competitividad (MINECO) and FEDER (CTQ2010-15358 and CTQ2013-48937-C2-1-P) and Junta de Castilla y Leon (BU237U13) for financial support. A.M.S. thanks the Junta de Castilla y Leon (Consejeria de Educacion) and the Fondo Social Europeo for a PIRTU contract. M.A.R. and P.G.-G. thank MEC for a "Young Foreign Researchers" (SB2009-0186) contract and MINECO for "Juan de la Cierva" contract, respectivelyen
dc.format.mimetypeapplication/pdf
dc.language.isoenges
dc.publisherWiley-VCH Verlagen
dc.relation.ispartofChemistry-A european journal. 2015. V. 21, n. 7, p. 3042-3052en
dc.subjectasymmetric catalysisen
dc.subjectcyclizationen
dc.subjectcycloisomerizationen
dc.subjectgolden
dc.subjectindenesen
dc.subject.otherQuímica orgánicaes
dc.subject.otherChemistry, Organicen
dc.titleGold(I)-Catalyzed Cycloisomerizations and Alkoxycyclizations of ortho-(Alkynyl)styrenesen
dc.typeinfo:eu-repo/semantics/article
dc.description.versionThis is the peer reviewed version of the following article: Sanjuán, A. M., Rashid, M. A., García-García, P., Martínez-Cuezva, A., Fernández-Rodríguez, M. A., Rodríguez, F. and Sanz, R. (2015), Gold(I)-Catalyzed Cycloisomerizations and Alkoxycyclizations of ortho-(Alkynyl)styrenes. Chem. Eur. J., 21: 3042–3052. doi: 10.1002/chem.201405789, which has been published in final form at 10.1002/chem.201405789. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving
dc.rights.accessRightsinfo:eu-repo/semantics/openAccess
dc.relation.publisherversionhttp://dx.doi.org/10.1002/chem.201405789
dc.identifier.doi10.1002/chem.201405789
dc.relation.projectIDinfo:eu-repo/grantAgreement/MINECO/CTQ2010-15358
dc.relation.projectIDinfo:eu-repo/grantAgreement/MINECO/CTQ2013-48937-C2-1-P
dc.relation.projectIDinfo:eu-repo/grantAgreement/MEC/SB2009-0186
dc.relation.projectIDinfo:eu-repo/grantAgreement/JCyL/BU237U13
dc.type.hasVersioninfo:eu-repo/semantics/acceptedVersionen


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