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Synlett 2000; 2000(4): 442-454
DOI: 10.1055/s-2000-6555
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Nucleophilic Additions to Chiral Nitrones: New Approaches to Nitrogenated Compounds

Pedro Merino* , Santiago Franco, Francisco L. Merchan, Tomas Tejero
  • *Departamento de Quimica Organica, ICMA, Facultad de Ciencias, Universidad de Zaragoza, E-50009 Zaragoza, Aragon, Spain; Fax +34 9 76 76 20 75; E-mail: pmerino@posta.unizar.es
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Publication Date:
31 December 2000 (online)

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The reaction of optically active α-alkoxy and α-amino nitrones with a variety of nucleophiles serves as a useful process for the stereocontrolled synthesis of enantiomerically pure hydroxylamines having additional functionalities. These hydroxylamines can be used as key intermediates in the synthesis of a wide range of nitrogenated compounds including amino acids, carbohydrates, nucleoside analogs and pyrrolidines.

nitrones - hydroxylamines - carbohydrates - nucleosides - amino acids