Palladium-catalyzed allylation and deacylative allylation of 3-acetyl-2-oxindoles with allylic alcohols

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dc.contributorSíntesis Asimétrica (SINTAS)es_ES
dc.contributor.authorOrtega-Martínez, Aitor-
dc.contributor.authorLorenzo, Rocco de-
dc.contributor.authorSansano, Jose M.-
dc.contributor.authorNájera, Carmen-
dc.contributor.otherUniversidad de Alicante. Departamento de Química Orgánicaes_ES
dc.contributor.otherUniversidad de Alicante. Instituto Universitario de Síntesis Orgánicaes_ES
dc.date.accessioned2017-12-20T10:27:13Z-
dc.date.available2017-12-20T10:27:13Z-
dc.date.issued2018-01-11-
dc.identifier.citationTetrahedron. 2018, 74(2): 253-259. doi:10.1016/j.tet.2017.11.041es_ES
dc.identifier.issn0040-4020 (Print)-
dc.identifier.issn1464-5416 (Online)-
dc.identifier.urihttp://hdl.handle.net/10045/72136-
dc.description.abstractThe Pd-catalyzed allylation of 3-acetyl-2-oxindoles with allyl alcohol is performed using 3 mol% of Pd(dba)2, rac-BINAP and BINOL phosphoric acid as catalytic mixture. This procedure allows the in situ synthesis of 3-allyl-2-oxindole by adding Triton B to the reaction mixture. The deacylative allylation of 3-acetyl-3-methyl-2-oxindoles with allylic alcohols is carried out with 3 mol% of Pd(OAc)2, dppp and 1.5 equiv. of LiOtBu as base affording the corresponding 3,3-disubstituted 2-oxindoles in good yields. Both methodologies can be combined for the preparation of unsymmetrical 3,3-diallylated 2-oxindoles such as compound 7. The DaA must be carried out in the absence of oxygen in order to avoid the competitive formation of 3-alkyl-3-hydroxy-2-indoles. The later compounds can be easily obtained by deacylative oxidation of 3-alkylated 3-acetyl-2-oxindoles with LiOEt at rt under air.es_ES
dc.description.sponsorshipWe gratefully acknowledge financial support from the Spanish Ministerio de Economía y Competitividad (MINECO) (projects CTQ2013-43446-P and CTQ2014-51912-REDC), the Spanish Ministerio de Economía, Industria y Competitividad, Agencia Estatal de Investigación (AEI) and Fondo Europeo de Desarrollo Regional (FEDER, EU) (projects CTQ2016-76782-P and CTQ2016-81797-REDC), the Generalitat Valenciana (PROMETEO2009/039 and PROMETEOII/2014/017) and the University of Alicante. A. O.-M. thanks MINECO for a predoctoral fellowship.es_ES
dc.languageenges_ES
dc.publisherElsevieres_ES
dc.rights© 2017 Elsevier Ltd.es_ES
dc.subjectOxindoleses_ES
dc.subjectAllylic alcoholses_ES
dc.subjectPalladiumes_ES
dc.subjectCatalysises_ES
dc.subjectDeacylationes_ES
dc.subject.otherQuímica Orgánicaes_ES
dc.titlePalladium-catalyzed allylation and deacylative allylation of 3-acetyl-2-oxindoles with allylic alcoholses_ES
dc.typeinfo:eu-repo/semantics/articlees_ES
dc.peerreviewedsies_ES
dc.identifier.doi10.1016/j.tet.2017.11.041-
dc.relation.publisherversionhttp://dx.doi.org/10.1016/j.tet.2017.11.041es_ES
dc.rights.accessRightsinfo:eu-repo/semantics/openAccesses_ES
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