An umpolung sulfoxide reagent for use as a functionalized benzyl carbanion equivalent (Articolo in rivista)

Type
Label
  • An umpolung sulfoxide reagent for use as a functionalized benzyl carbanion equivalent (Articolo in rivista) (literal)
Anno
  • 2011-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1016/j.tet.2011.05.033 (literal)
Alternative label
  • Pinna, Giovanni; Bellucci, Maria Cristina; Malpezzi, Luciana; Pisani, Laura; Superchi, Stefano; Volonterio, Alessandro; Zanda, Matteo (2011)
    An umpolung sulfoxide reagent for use as a functionalized benzyl carbanion equivalent
    in Tetrahedron (Oxf., Print)
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Pinna, Giovanni; Bellucci, Maria Cristina; Malpezzi, Luciana; Pisani, Laura; Superchi, Stefano; Volonterio, Alessandro; Zanda, Matteo (literal)
Pagina inizio
  • 5268 (literal)
Pagina fine
  • 5281 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume
  • 67 (literal)
Rivista
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#pagineTotali
  • 14 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroFascicolo
  • 29 (literal)
Note
  • ISI Web of Science (WoS) (literal)
  • ISI Web of Science (WOS) (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • Polytechnic University of Milan; University of Milan; University of Basilicata; CNR ICRM; University of Aberdeen (literal)
Titolo
  • An umpolung sulfoxide reagent for use as a functionalized benzyl carbanion equivalent (literal)
Abstract
  • N-Methyl ortho-carbamoylaryl benzyl sulfoxides can be used as synthetic equivalents for alpha-hydroxy, alpha-chloro, and alpha-acetammido benzyl carbanions by means of a two-step sequence involving highly diastereoselective alpha-C-alkylation with alkyl halides followed by displacement of the sulfinyl residue (which can be recovered and recycled) by a hydroxyl, a chlorine or an acetamido, respectively, under non-oxidative Pummerer conditions. The scope and limits of the method, including a stereoselective version of the reaction, as well as the mechanism of the process are discussed in detail. (C) 2011 Elsevier Ltd. All rights reserved. (literal)
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