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Synlett 2001; 2001(8): 1281-1283
DOI: 10.1055/s-2001-16042
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One-Pot Synthesis of Functionalized Nitrones from Nitro Compounds

Valérie Gautheron-Chapoulaud* , Shashi U. Pandya, Pascale Cividino, Géraldine Masson, Sandrine Py, Yannick Vallée
  • *LEDSS, UMR CNRS-Université Joseph Fourier, B.P.53X, 38041 Grenoble, France; Fax + 33 (4) 76 51 43 82; E-mail: yannick.vallee@ujf-grenoble.fr
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Publication Date:
31 December 2001 (online)

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The zinc-mediated reduction of nitroalkanes and nitroarenes in the presence of aldehydes is an efficient method to synthesize a wide range of nitrones. This method is mild enough to accommodate a variety of functional groups. It is particularly useful when the intermediate hydroxylamines are unstable and/or water-soluble. We used it to prepare several aromatic, aliphatic and highly functionalized sugar-derived nitrones.

zinc reductions - nitro derivatives - hydroxylamines - carbohydrate derivatives - nitrones