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Highly Diastereoselective Multicomponent Synthesis of Spirocyclopropyl Oxindoles Enabled by Rare-Earth Metal Salts

dc.contributor.authorTallarida, Matteo A.
dc.contributor.authorOlivito, Fabrizio
dc.contributor.authorNavo, Claudio D.
dc.contributor.authorAlgiero, Vincenzo
dc.contributor.authorJiritano, Antonio
dc.contributor.authorCostanzo, Paola
dc.contributor.authorPoveda, Ana
dc.contributor.authorMoure, Maria J.
dc.contributor.authorJiménez Barbero, Jesús ORCID
dc.contributor.authorMaiuolo, Loredana
dc.contributor.authorJiménez Oses, Gonzalo
dc.contributor.authorDe Nino, Antonio
dc.date.accessioned2023-05-15T14:58:26Z
dc.date.available2023-05-15T14:58:26Z
dc.date.issued2023-04
dc.identifier.citationOrganic Letters 25(17) : 3001-3006 (2023)es_ES
dc.identifier.issn1523-7052
dc.identifier.urihttp://hdl.handle.net/10810/61116
dc.description.abstractThe synthesis of polysubstituted spirocyclopropyl oxindoles using a series of rare-earth metal (REM) salts is reported. REMs, in particular Sc(OTf)3, allowed access to the target compounds by a multicomponent reaction with high diastereoselectivity (≤94:6:0:0). Density functional theory calculations on the model reaction are consistent with the observed selectivity and revealed that the special coordinating capabilities and the oxophilicity of the metal are key factors in inducing the formation of one main diastereoisomer.es_ES
dc.description.sponsorshipThe authors thank Diana Cabrera, Sebastiaan van Liempd, and Juan M. Falcon-Perez from the CIC bioGUNE Metabolomics Platform for performing the UPLC-MS/MS analyses. The authors also acknowledge the Italian Ministry of University and Research (MUR) for Project SI.F.I.PA.CRO.DE. - Sviluppo e industrializzazione farmaci innovativi per terapia molecolare personalizzata PA.CRO.DE. (PON ARS01_00568, CUP: B29C20000360005) and for two doctoral grants. Moreover, the authors thank the University of Calabria and Calabria Region (PAC CALABRIA 2014–2020-Asse Prioritario 12, Azione B 10.5.12 CUP: H28D19000040006) for financial support. This research was also funded by MCIN/AEI/10.13039/501100011033 (Grant PID2021-125946OB-I00 to G.J.-O. and Severo Ochoa Excellence Accreditation CEX2021-001136-S to CIC bioGUNE).es_ES
dc.language.isoenges_ES
dc.publisherAmerican Chemical Societyes_ES
dc.relationinfo:eu-repo/grantAgreement/MICINN/PID2021-125946OB-I00es_ES
dc.relationinfo:eu-repo/grantAgreement/MICINN/CEX2021-001136-Ses_ES
dc.rightsinfo:eu-repo/semantics/openAccesses_ES
dc.rights.urihttp://creativecommons.org/licenses/by/3.0/es/*
dc.titleHighly Diastereoselective Multicomponent Synthesis of Spirocyclopropyl Oxindoles Enabled by Rare-Earth Metal Saltses_ES
dc.typeinfo:eu-repo/semantics/articlees_ES
dc.rights.holder© 2023 The Authors. Published by American Chemical Society. Attribution 4.0 International (CC BY 4.0)es_ES
dc.rights.holderAtribución 3.0 España*
dc.relation.publisherversionhttps://pubs.acs.org/doi/10.1021/acs.orglett.3c00772es_ES
dc.identifier.doi10.1021/acs.orglett.3c00772
dc.departamentoesQuímica Orgánica e Inorgánicaes_ES
dc.departamentoeuKimika Organikoa eta Ez-Organikoaes_ES


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© 2023 The Authors. Published by American Chemical Society. Attribution 4.0 International (CC BY 4.0)
Except where otherwise noted, this item's license is described as © 2023 The Authors. Published by American Chemical Society. Attribution 4.0 International (CC BY 4.0)