Bis-enolates with extended π-conjugation are powerful nucleophiles. Study of their alkylation reactions with very hindered C-electrophiles

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dc.contributor.affiliationUniversidade de Santiago de Compostela. Centro de Investigación en Química Biolóxica e Materiais Moleculareses_ES
dc.contributor.authorCastroagudín Campos, Mariña
dc.contributor.authorLobato, Rubén
dc.contributor.authorMartínez García, Lucas
dc.contributor.authorSardina López, Francisco Javier
dc.contributor.authorPaleo Pillado, María Rita
dc.date.accessioned2024-02-06T08:05:38Z
dc.date.available2024-02-06T08:05:38Z
dc.date.issued2019
dc.descriptionThis document is the Accepted Manuscript version of a Published Work that appeared in final form in The Journal of Organic Chemistry, copyright © 2019 American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.joc.9b01961es_ES
dc.description.abstractBis-enolates with extended π-conjugation, prepared by alkali metal-mediated reduction of several aromatic and unsaturated diesters, can be efficiently and regioselectively alkylated with very hindered C-electrophiles, such as neopentyl, secondary and tertiary alkyl halides, and tosylates. A one-step synthesis of 4-alkyl phthalates was derived from the reductive alkylation of a phthalate diester with hindered halides followed by rearomatization with oxygen. Additionally, synthetic protocols have been developed to efficiently prepare complex fused- or spiro-bicycles from diisopropyl phthalate in just one or two stepses_ES
dc.description.peerreviewedSIes_ES
dc.description.sponsorshipFinancial support from Ministerio de Economía y Competitividad of Spain (CTQ2017-84354-P), Xunta de Galicia (GRC 2014/029 and Centro singular de investigación de Galicia accreditation 2016-2019, ED431G/09), and the European Union (European Regional Development Fund-ERDF) is gratefully acknowledged.es_ES
dc.identifier.citationCastroagudín, M.,Lobato, R., Martínez García, L., Sardina, F.J., Paleo, M.R. (2019). Bis-enolates with extended π-conjugation are powerful nucleophiles. Study of their alkylation reactions with very hindered C-electrophiles. "The journal of organic chemistry", vol.84, 15805-15816es_ES
dc.identifier.doi10.1021/acs.joc.9b01961
dc.identifier.essn1520-6904
dc.identifier.issn1361-1378
dc.identifier.urihttp://hdl.handle.net/10347/32383
dc.language.isoenges_ES
dc.publisherThe American Chemical Societyes_ES
dc.relation.projectIDinfo:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2017-84354-P/ES/CONTROL DE LA AFINIDAD, DINAMICA Y ESTRUCTURA DE SISTEMAS SUPRAMOLECULARES AUTOAGREGADOS/es_ES
dc.relation.projectIDinfo:eu-repo/grantAgreement/EC/H2020/676627/EUes_ES
dc.relation.publisherversionhttps://doi.org/10.1021/acs.joc.9b01961es_ES
dc.rightsCopyright © 2019 American Chemical Societyes_ES
dc.rights.accessRightsopen accesses_ES
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/4.0/
dc.subjectAlcoholses_ES
dc.subjectAnionses_ES
dc.subjectElectrophileses_ES
dc.subjectOrganic compoundses_ES
dc.subject.classification2306 Química orgánicaes_ES
dc.subject.classification2415 Biología moleculares_ES
dc.titleBis-enolates with extended π-conjugation are powerful nucleophiles. Study of their alkylation reactions with very hindered C-electrophileses_ES
dc.typejournal articlees_ES
dc.type.hasVersionAMes_ES
dspace.entity.typePublication
relation.isAuthorOfPublicationd2ead1ad-132f-4d2d-9aff-5d8afd8237c9
relation.isAuthorOfPublicationff51de10-efdc-4fd3-9fab-8f2ab82f663b
relation.isAuthorOfPublication.latestForDiscoveryd2ead1ad-132f-4d2d-9aff-5d8afd8237c9

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