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dc.contributor.authorCagiao Marcote, David
dc.contributor.authorVarela Sandá, Iván
dc.contributor.authorFernández Casado, Jaime
dc.contributor.authorMascareñas Cid, José Luis
dc.contributor.authorLópez García, Fernando
dc.date.accessioned2019-03-21T14:26:55Z
dc.date.available2019-11-07T02:00:10Z
dc.date.issued2018
dc.identifier.citationMarcote, D., Varela, I., Fernández-Casado, J., Mascareñas, J., & López, F. (2018). Gold(I)-Catalyzed Enantioselective Annulations between Allenes and Alkene-Tethered Oxime Ethers: A Straight Entry to Highly Substituted Piperidines and aza-Bridged Medium-Sized Carbocycles. Journal Of The American Chemical Society, 140(48), 16821-16833. doi: 10.1021/jacs.8b10388
dc.identifier.issn0002-7863
dc.identifier.urihttp://hdl.handle.net/10347/18461
dc.descriptionNOTICE: This is the peer reviewed version of the following article: Marcote, D. C., Varela, I., Fernández-Casado, J., Mascareñas, J.L., López*, F. (2019), Gold(I)–catalyzed enantioselective annulations between allenes and alkene-tethered oxime ethers: A straight entry to highly substituted piperidines and aza-bridged medium-sized carbocycles. J. Am. Chem. Soc., 140, 16821-16833 [doi: 10.1021/jacs.8b10388]. This article may be used for non-commercial purposes in accordance with ACS Terms and Conditions for self-archiving
dc.description.abstractPiperidine scaffolds are present in a wide range of bioactive natural products and are therefore considered as highly valuable, privileged synthetic targets. In this manuscript, we describe a gold-catalyzed annulation strategy that allows a straightforward assembly of piperidines and piperidine-containing aza-bridged products from readily available alkene-tethered oxime ethers (or esters) and N-allenamides. Importantly, we demonstrate the advantages of using oxime derivatives over imines, something pertinent to the whole area of gold catalysis, and provide relevant mechanistic experiments that shed light into the factors affecting the annulation processes. Moreover, we also describe preliminary experiments demonstrating the viability of enantioselective versions of the above reactions
dc.description.sponsorshipThis work received financial support from the Spanish MINECO (SAF2016-76689-R, CTQ2017-84767-P, FPU fellowship to I.V. and J.F.-C.), the Xunta de Galicia (ED431C 2017/19, 2015-CP082, Centro Singular de Investigacion de Galicia accreditation 2016-2019 ED431G/09 and ́ predoctoral fellowship to D.C.M.), the ERDF, ERC (Adv. Grant No. 340055), and the Orfeo-Cinqa network (CTQ2016- 81797-REDC). Dr. Rebeca Garcí a-Fandiño is acknowledged for her contribution to the DFT studies
dc.language.isoeng
dc.publisherAmerican Chemical Society
dc.relationinfo:eu-repo/grantAgreement/EC/FP7/340055
dc.relationinfo:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/SAF2016-76689-R/ES
dc.relationinfo:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/CTQ2017-84767-P/ES/METODOS SINTETICOS EFICIENTES BASADOS EN CATALISIS METALICA. DESARROLLOS ENANTIOSELECTIVOS Y ACCESO A MOLECULAS BIOACTIVAS Y/O DE ALTO INTERES SINTETICO
dc.rights© 2018 American Chemical Society. This article may be used for non-commercial purposes in accordance with ACS Terms and Conditions for self-archiving
dc.titleGold(I)–catalyzed enantioselective annulations between allenes and alkene-tethered oxime ethers: A straight entry to highly substituted piperidines and aza-bridged medium-sized carbocycles
dc.typeinfo:eu-repo/semantics/article
dc.identifier.DOI10.1021/jacs.8b10388
dc.relation.publisherversionhttps://doi.org/10.1021/jacs.8b10388
dc.type.versioninfo:eu-repo/semantics/acceptedVersion
dc.identifier.e-issn1520-5126
dc.rights.accessrightsinfo:eu-repo/semantics/openAccess
dc.contributor.affiliationUniversidade de Santiago de Compostela. Centro de Investigación en Química Biolóxica e Materiais Moleculares
dc.contributor.affiliationUniversidade de Santiago de Compostela. Departamento de Química Orgánica
dc.description.peerreviewedSI


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