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Hydroalumination of seleno acetylenes: a versatile generation and reactions of alpha-aluminate vinyl selenide intermediates in the highly regio and stereoselective synthesis of telluro(seleno)ketene acetals

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dc.contributor.authorGuerrero, Palimclo G. [UNESP]
dc.contributor.authorDabdoub, Miguel J.
dc.contributor.authorBaroni, Adriano C. M.
dc.contributor.institutionUniversidade Estadual Paulista (Unesp)
dc.contributor.institutionUniversidade de São Paulo (USP)
dc.contributor.institutionUniversidade Federal de Mato Grosso do Sul (UFMS)
dc.date.accessioned2014-05-20T13:12:07Z
dc.date.available2014-05-20T13:12:07Z
dc.date.issued2008-06-09
dc.description.abstractThe hydroalumination of butylseleno acetylenes with DIBAL-H followed by addition of n-butyllithium generated in situ the (Z)-butylseleno vinyl alanates intermediates which were captured with C(4)H(9)TeBr furnishing the (E)-telluro(seleno)ketene acetals exclusively. The isomers with opposite stereochemistry (Z)-telluro(seleno)ketene acetals were obtained by the reduction of phenylseleno acetylenes with lithium di-(isobutyl)-n-butyl aluminate hydride (Zweifel's reagent) followed by reaction of (E)-phenylseleno vinyl alanates intermediates with C(4)H(9)TeBr. (c) 2008 Elsevier Ltd. All rights reserved.en
dc.description.affiliationUNESP, Lab Quim Organ, BR-11900000 Registro, SP, Brazil
dc.description.affiliationUSP, Lab Compostos Organocalcogenios, BR-14500000 Ribeirao Preto, Brazil
dc.description.affiliationUniversidade Federal de Mato Grosso do Sul (UFMS), Quim Farmaceut Lab, Campo Grande, MS, Brazil
dc.description.affiliationUnespUNESP, Lab Quim Organ, BR-11900000 Registro, SP, Brazil
dc.format.extent3872-3876
dc.identifierhttp://dx.doi.org/10.1016/j.tetlet.2008.04.072
dc.identifier.citationTetrahedron Letters. Oxford: Pergamon-Elsevier B.V. Ltd, v. 49, n. 24, p. 3872-3876, 2008.
dc.identifier.doi10.1016/j.tetlet.2008.04.072
dc.identifier.issn0040-4039
dc.identifier.urihttp://hdl.handle.net/11449/110
dc.identifier.wosWOS:000256500500009
dc.language.isoeng
dc.publisherPergamon-Elsevier B.V. Ltd
dc.relation.ispartofTetrahedron Letters
dc.relation.ispartofjcr2.125
dc.relation.ispartofsjr0,683
dc.rights.accessRightsAcesso restrito
dc.sourceWeb of Science
dc.titleHydroalumination of seleno acetylenes: a versatile generation and reactions of alpha-aluminate vinyl selenide intermediates in the highly regio and stereoselective synthesis of telluro(seleno)ketene acetalsen
dc.typeArtigo
dcterms.licensehttp://www.elsevier.com/about/open-access/open-access-policies/article-posting-policy
dcterms.rightsHolderPergamon-Elsevier B.V. Ltd
dspace.entity.typePublication
unesp.campusUniversidade Estadual Paulista (UNESP), Faculdade de Ciências Agrárias do Vale do Ribeira, Registropt
unesp.departmentEngenharia Agronômica - FCAVRpt

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