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Synthesis 1996; 1996(5): 627-632
DOI: 10.1055/s-1996-4257
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Diastereoselective Synthesis of Branched-Chain Cyanonitrosugar Derivatives by Michael Addition/MMPP Oxidation Using Formaldehyde SAMP- and RAMP-Hydrazones as New Chiral Cyanide Equivalents

Rosario Fernández, Consolación Gasch, Jose-María Lassaletta* , José-Manuel LLera
  • *Departamento de Química Orgánica, Facultad de Química, Universidad de Sevilla, Apartado de Correos No. 553, E-41071, Seville, Spain, Fax +34(5)4624960
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Publication Date:
31 December 2000 (online)

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The diastereoselective synthesis of sugar derived β-nitro nitriles through double asymmetric induction experiments involving Michael addition of formaldehyde SAMP- and RAMP-hydrazones [(S)-1 and (R)-1] to sugar nitroolefins 2 in excellent overall yields and high diastereoselective excesses is described. The absolute configuration of the RAMP-hydrazone 1,4-adduct 3c was determined by chemical correlation of its corresponding β-nitro nitrile 4c.

chiral cyanide equivalent - Michael addition - double asymmetric induction - branched sugars - formaldehyde SAMP/RAMP-hydrazones