Highly Enantioselective Iridium(I)-Catalyzed Hydrocarbonation of Alkenes: A Versatile Approach to Heterocyclic Systems Bearing Quaternary Stereocenters

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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.authorArribas Domingo, Andrés
dc.contributor.authorCalvelo Souto, Martín
dc.contributor.authorFernández Fernández, David
dc.contributor.authorRodrigues, Catarina A. B.
dc.contributor.authorMascareñas Cid, José Luis
dc.contributor.authorLópez García, Fernando
dc.date.accessioned2021-07-27T13:23:50Z
dc.date.available2021-07-27T13:23:50Z
dc.date.issued2021
dc.description.abstractWe report a versatile, highly enantioselective intramolecular hydrocarbonation reaction that provides a direct access to heteropolycyclic systems bearing chiral quaternary carbon stereocenters. The method, which relies on an iridium(I)/bisphosphine chiral catalyst, is particularly efficient for the synthesis of five-, six- and seven-membered fused indole and pyrrole products, bearing one and two stereocenters, with enantiomeric excesses of up to >99 %. DFT computational studies allowed to obtain a detailed mechanistic profile and identify a cluster of weak non-covalent interactions as key factors to control the enantioselectivitygl
dc.description.peerreviewedSIgl
dc.description.sponsorshipThis work received financial support from the Spanish MINECO (SAF2016-76689-R, PID2019-108624RB-I00, CTQ2017-84767-P, PID2020-118579GB-I00), the Xunta de Galicia (ED431C 2017/19, 2015-CP082, Centro Singular de Investigación de Galicia accreditation 2019-2022, ED431G 2019/03, a predoctoral Fellowship to A. A. and M. C. and a postdoctoral Fellowship to D. F. F, ED481B-2019-005) and the ERDF, ERC (Adv. Grant No. 340055). The Orfeo-Cinqa network (CTQ2016-81797-REDC)gl
dc.identifier.citationArribas, A., Calvelo, M., Fernández, D.F., Rodrigues, C.A.B., Mascareñas, J.L. and López, F. (2021), Highly Enantioselective Iridium(I)-Catalyzed Hydrocarbonation of Alkenes: A Versatile Approach to Heterocyclic Systems Bearing Quaternary Stereocenters. Angew. Chem. Int. Ed.. https://doi.org/10.1002/anie.202105776gl
dc.identifier.doi10.1002/anie.202105776
dc.identifier.essn1521-3773
dc.identifier.issn1433-7851
dc.identifier.urihttp://hdl.handle.net/10347/26623
dc.language.isoenggl
dc.publisherWileygl
dc.relation.projectIDinfo:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/SAF2016-76689-R/ESgl
dc.relation.projectIDinfo:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2019-108624RB-I00/ES/HERRAMIENTAS BASADAS EN METALES PARA SU USO EN QUIMICA BIOLOGICA Y BIOMEDICINA. DESARROLLO DE NUEVAS ESTRATEGIAS ANTICANCERgl
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 SINTETICOgl
dc.relation.projectIDinfo:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2020-118579GB-I00/ESgl
dc.relation.projectIDinfo:eu-repo/grantAgreement/EC/FP7/340055gl
dc.relation.publisherversionhttps://doi.org/10.1002/anie.202105776gl
dc.rights© 2021 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH. This is an open access article under the terms of the Creative Commons Attribution-NonCommercial-NoDerivs License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non-commercial and no modifications or adaptations are madegl
dc.rightsAttribution-NonCommercial-NoDerivatives 4.0 Internacional
dc.rights.accessRightsopen accessgl
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/4.0/
dc.subjectC-H activationgl
dc.subjectEnantioselectivegl
dc.subjectHeterocyclesgl
dc.subjectHydrocarbonationgl
dc.subjectIridiumgl
dc.titleHighly Enantioselective Iridium(I)-Catalyzed Hydrocarbonation of Alkenes: A Versatile Approach to Heterocyclic Systems Bearing Quaternary Stereocentersgl
dc.typejournal articlegl
dc.type.hasVersionVoRgl
dspace.entity.typePublication
relation.isAuthorOfPublicationdd645598-c57c-4276-88fd-6933845cb9b2
relation.isAuthorOfPublication5ae222c9-f626-432b-aac5-da78c06ed64f
relation.isAuthorOfPublication.latestForDiscoverydd645598-c57c-4276-88fd-6933845cb9b2

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