Diastereoselective synthesis of branched-chain cyanonitrosugar derivatives by Michael addition/MMPP oxidation using formaldehyde SAMP- and RAMP-hydrazones as new chiral cyanide equivalents

Article abstract of DOI:10.1055/s-1996-4257

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.