Kinetic Resolution of Allyltriflamides through a Pd-Catalyzed C–H Functionalization with Allenes: Asymmetric Assembly of Tetrahydropyridines

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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.authorGonzález González, José Manuel
dc.contributor.authorCendón Mariño, Borja
dc.contributor.authorMascareñas Cid, José Luis
dc.contributor.authorGulías Costa, Moisés
dc.date.accessioned2021-03-22T08:56:38Z
dc.date.issued2021
dc.description.abstractEnantioenriched, six-membered azacycles are essential structural motifs in many products of pharmaceutical or agrochemical interest. Here we report a simple and practical method for enantioselective assembly of tetrahydropyridines, which is paired to a kinetic resolution of α-branched allyltriflamides. The reaction consists of a formal (4+2) cycloaddition between the allylamine derivatives and allenes and is initiated by a palladium(II)-catalyzed C–H activation process. Both the chiral allylamide precursors and the tetrahydropyridine adducts were successfully obtained in high yields, with excellent enantioselectivity (up to 99% ee) and selectivity values of up to 127gl
dc.description.peerreviewedSIgl
dc.description.sponsorshipThis work has received financial support from Spanish grants (SAF2016-76689-R, CTQ2016-77047-P, PID2019-108624RBI00, PID2019-110385GB-I00, and FPI fellowship to B.C.), the Consellería de Cultura, Educación e Ordenación Universitaria (ED431C 2017/19, 2015-CP082 and Centro Singular de Investigación de Galicia accreditation 2019-2022, ED431G 2019/03 and J. M. G fellowship), the European Regional Development Fund (ERDF), and the European Research Council (Advanced Grant No. 340055). The orfeo-cinqa network CTQ2016-81797-REDC is also kindly acknowledgedgl
dc.identifier.citationJ. Am. Chem. Soc. 2021, 143, 10, 3747–3752gl
dc.identifier.doi10.1021/jacs.1c01929
dc.identifier.essn1520-5126
dc.identifier.issn0002-7863
dc.identifier.urihttp://hdl.handle.net/10347/24850
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/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2016-81797-REDC/ES
dc.relation.projectIDinfo:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2019-110385GB-I00/ES/NUEVOS METODOS DE SINTESIS QUIMICA MEDIANTE LA FUNCIONALIZACION DE ENLACES C-H CON CATALIZADORES METALICOS
dc.relation.publisherversionhttps://doi.org/10.1021/jacs.1c01929gl
dc.rights© 2021 American Chemical Society. This is an open access article under the CC Attribution 4.0 International (CC BY 4.0) license (http://creativecommons.org/licenses/by/4.0/)gl
dc.rights.accessRightsopen accessgl
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/
dc.titleKinetic Resolution of Allyltriflamides through a Pd-Catalyzed C–H Functionalization with Allenes: Asymmetric Assembly of Tetrahydropyridinesgl
dc.typejournal articlegl
dc.type.hasVersionVoRgl
dspace.entity.typePublication
relation.isAuthorOfPublication5ae222c9-f626-432b-aac5-da78c06ed64f
relation.isAuthorOfPublication47a6a088-27a9-412e-8422-0de4fd8af0d4
relation.isAuthorOfPublication.latestForDiscovery5ae222c9-f626-432b-aac5-da78c06ed64f

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