Petit Roig, ElenaBosch Hereu, LluísFont, JoanMola Solà, LauraCosta i Arnau, Anna M.Vilarrasa i Llorens, Jaume2015-02-202015-08-272014-08-270022-3263https://hdl.handle.net/2445/63194The 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.22 p.application/pdfeng(c) American Chemical Society , 2014EstereoquímicaCompostos heterocíclicsCatàlisiSíntesi orgànicaProves i reactius químicsStereochemistryHeterocyclic compoundsCatalysisOrganic synthesisChemical tests and reagentsinfo:eu-repo/semantics/article6469262015-02-20info:eu-repo/semantics/openAccess