Diastereoselective Synthesis of Branched-Chain Cyanonitrosugar Derivatives by Michael Addition/MMPP Oxidation Using Formaldehyde SAMP- and RAMP-Hydrazones as New Chiral Cyanide Equivalents
- 1 May 1996
- journal article
- research article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 1996 (05) , 627-632
- https://doi.org/10.1055/s-1996-4257
Abstract
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.Keywords
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