Please use this identifier to cite or link to this item:
Full metadata record
DC FieldValueLanguage
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.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.publisherAmerican Chemical Society-
dc.relation.isformatofVersió postprint del document publicat a:
dc.relation.ispartofJournal of Organic Chemistry, 2014, vol. 79, num. 18, p. 8826-8834-
dc.rights(c) American Chemical Society , 2014-
dc.subject.classificationCompostos heterocíclics-
dc.subject.classificationSíntesi orgànica-
dc.subject.classificationProves i reactius químics-
dc.subject.otherHeterocyclic compounds-
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.-
Appears in Collections:Articles publicats en revistes (Química Inorgànica i Orgànica)

Files in This Item:
File Description SizeFormat 
646926.pdf518.8 kBAdobe PDFView/Open

Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.