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dc.contributor.authorMarcote, D. C.-
dc.contributor.authorVarela, I.-
dc.contributor.authorFernández-Casado, J.-
dc.contributor.authorMascarenas, J. L.-
dc.contributor.authorLópez, Fernando-
dc.identifierdoi: 10.1021/jacs.8b10388-
dc.identifierissn: 0002-7863-
dc.identifiere-issn: 1520-5126-
dc.identifier.citationJournal of the American Chemical Society 140: 16821-16833 (2018)-
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 Investigación 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 Garciá -Fandiño is acknowledged for her contribution to the DFT studies.-
dc.publisherAmerican Chemical Society-
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.description.versionPeer Reviewed-
dc.contributor.funderMinisterio de Economía y Competitividad (España)-
dc.contributor.funderMinisterio de Ciencia, Innovación y Universidades (España)-
dc.contributor.funderXunta de Galicia-
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