Enantioselective Palladium-Catalyzed [3C + 2C] and [4C + 3C] Intramolecular Cycloadditions of Alkylidenecyclopropanes

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dc.contributor.affiliationUniversidade de Santiago de Compostela. Centro de Investigación en Química Biolóxica e Materiais Molecularesgl
dc.contributor.affiliationUniversidade de Santiago de Compostela. Departamento de Química Orgánicagl
dc.contributor.authorVerdugo Leal, Felipe Ignacio
dc.contributor.authorVillarino Palmaz, Lara
dc.contributor.authorDurán, Juan
dc.contributor.authorGulías Costa, Moisés
dc.contributor.authorMascareñas Cid, José Luis
dc.contributor.authorLópez García, Fernando
dc.date.accessioned2018-10-08T12:17:44Z
dc.date.available2018-12-04T02:00:09Z
dc.date.issued2018-06-04
dc.descriptionNOTICE: This is the peer reviewed version of the following article: Felipe Verdugo, Lara Villarino, Juan Durán, Moisés Gulías, José L. Mascareñas and Fernando López (2018), Enantioselective Palladium-Catalyzed [3C + 2C] and [4C + 3C] Intra-molecular Cycloadditions of Alkylidenecyclopropanes. ACS Catalysis, 2018, 8, 6100–6105 [DOI: 10.1021/acscatal.8b01296]. This article may be used for non-commercial purposes in accordance with American Chemical Society Terms and Conditions for self-archivinggl
dc.description.abstractWe report a highly enantioselective [3C + 2C] intramolecular cycloaddition of alkylidenecyclopropanes (ACPs) and alkenes. The best results are obtained by using sterically demanding chiral phosphoramidite ligands derived from Vapol. Moreover, we also show that related, but less bulky, phosphoramidites can also lead to very effective [4C + 3C] cycloadditions when dienes, instead of alkenes, are used as reacting partners. The reactions provide a practical, simple, and selective access to optically active, synthetically appealing 5,5- and 5,7-bicyclic systemsgl
dc.description.peerreviewedSIgl
dc.description.sponsorshipThis work received financial support from the spanish MINECO grants (Nos. SAF2016-76689-R, CTQ2016-77047-P, CTQ2017-84767-P, FPU to L.V. and J.D.), Xunta de Galicia (Nos. ED431C 2017/19, 2015-CP082, and Centro Singular de Investigación de Galicia accreditation 2016-2019 ED431G/09), the ERDF and ERC (Adv. Grant No. 340055). The Orfeo-Cinqa network CTQ2016-81797-REDC, CONICYT-Becas Chile (Ph.D. grant to F.V.) and Sarah Walker (preliminary work) are also acknowledgedgl
dc.identifier.citationVerdugo, F., Villarino, L., Durán, J., Gulías, M., Mascareñas, J., & López, F. (2018). Enantioselective Palladium-Catalyzed [3C + 2C] and [4C + 3C] Intramolecular Cycloadditions of Alkylidenecyclopropanes. ACS Catalysis, 8(7), 6100-6105. doi: 10.1021/acscatal.8b01296gl
dc.identifier.doi10.1021/acscatal.8b01296
dc.identifier.issn2155-5435
dc.identifier.urihttp://hdl.handle.net/10347/17410
dc.language.isoenggl
dc.publisherAmerican Chemical Societygl
dc.relation.projectIDinfo:eu-repo/grantAgreement/EC/FP7/340055
dc.relation.projectIDinfo:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2016-81797/ES
dc.relation.projectIDinfo:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/SAF2016-76689-R/ES
dc.relation.projectIDinfo: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.relation.projectIDinfo:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2016-81797-REDC/ES
dc.relation.publisherversionhttps://doi.org/10.1021/acscatal.8b01296gl
dc.rights© 2018 American Chemical Societygl
dc.rights.accessRightsopen accessgl
dc.subjectAlkylidenecyclopropanegl
dc.subjectAsymmetricgl
dc.subjectCycloadditiongl
dc.subjectEnantioselectivegl
dc.subjectPalladiumgl
dc.subjectPhosphoramiditegl
dc.titleEnantioselective Palladium-Catalyzed [3C + 2C] and [4C + 3C] Intramolecular Cycloadditions of Alkylidenecyclopropanesgl
dc.typejournal articlegl
dc.type.hasVersionAMgl
dspace.entity.typePublication
relation.isAuthorOfPublication08e9d7b3-78e4-4dd1-9f4b-4d65a675c331
relation.isAuthorOfPublication47a6a088-27a9-412e-8422-0de4fd8af0d4
relation.isAuthorOfPublication5ae222c9-f626-432b-aac5-da78c06ed64f
relation.isAuthorOfPublication.latestForDiscovery08e9d7b3-78e4-4dd1-9f4b-4d65a675c331

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