Please use this identifier to cite or link to this item: http://hdl.handle.net/2445/63194
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dc.contributor.authorPetit, Elena-
dc.contributor.authorBosch Hereu, Lluís-
dc.contributor.authorFont, Joan-
dc.contributor.authorMola Solà, Laura-
dc.contributor.authorCosta i Arnau, Anna M.-
dc.contributor.authorVilarrasa i Llorens, Jaume-
dc.date.accessioned2015-02-20T12:19:49Z-
dc.date.available2015-08-27T22:01:40Z-
dc.date.issued2014-08-27-
dc.identifier.issn0022-3263-
dc.identifier.urihttp://hdl.handle.net/2445/63194-
dc.description.abstractThe use of the 2-(4-methylphenylsulfonyl)ethenyl (tosvinyl, Tsv) group for the protection of the NH group of a series of imides, azinones (including AZT), inosines, and cyclic sulfonamides has been examined. The Tsv-protected derivatives are obtained in excellent yields by conjugate addition to tosylacetylene (ethynyl p-tolyl sulfone). The stereochemistry of the double bond can be controlled at will: with only 1 mol % of Et3N or with catalytic amounts of NaH, the Z stereoisomers are generated almost exclusively, while the E isomers are obtained using a stoichiometric amount of DMAP. Analogous phenylsulfonylvinyl-protected groups (with the besvinyl or Bsv group instead of Tsv) are obtained stereospecifically by reaction with (Z)- or (E)-bis(phenylsulfonyl)ethene. For lactams and oxazolidinones, this last method is much better. The Tsv and Bsv groups are stable in the presence of non-nucleophilic bases and to acids. They can be removed highly effectively via a conjugate addition-elimination mechanism using pyrrolidine or sodium dodecanethiolate as nucleophiles.-
dc.format.extent22 p.-
dc.format.mimetypeapplication/pdf-
dc.language.isoeng-
dc.publisherAmerican Chemical Society-
dc.relation.isformatofVersió postprint del document publicat a: http://dx.doi.org/10.1021/jo501647w-
dc.relation.ispartofJournal of Organic Chemistry, 2014, vol. 79, num. 18, p. 8826-8834-
dc.relation.urihttp://dx.doi.org/10.1021/jo501647w-
dc.rights(c) American Chemical Society , 2014-
dc.subject.classificationEstereoquímica-
dc.subject.classificationCompostos heterocíclics-
dc.subject.classificationCatàlisi-
dc.subject.classificationSíntesi orgànica-
dc.subject.classificationProves i reactius químics-
dc.subject.otherStereochemistry-
dc.subject.otherHeterocyclic compounds-
dc.subject.otherCatalysis-
dc.subject.otherOrganic synthesis-
dc.subject.otherChemical tests and reagents-
dc.titleTosvinyl and besvinyl as protecting groups of imides, azinones, nucleosides, sultams, and lactams. Catalytic conjugate additions to tosylacetylene.-
dc.typeinfo:eu-repo/semantics/article-
dc.typeinfo:eu-repo/semantics/acceptedVersion-
dc.identifier.idgrec646926-
dc.date.updated2015-02-20T12:19:49Z-
dc.rights.accessRightsinfo:eu-repo/semantics/openAccess-
Appears in Collections:Articles publicats en revistes (Química Inorgànica i Orgànica)

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