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  • Title: One-pot enantioselective syntheses of iminosugar derivatives using organocatalytic anti-michael-anti-aza-Henry reactions.
    Author: Imashiro R, Uehara H, Barbas CF.
    Journal: Org Lett; 2010 Nov 19; 12(22):5250-3. PubMed ID: 21033702.
    Abstract:
    Organocatalyst-controlled asymmetric anti-Michael reactions of (tert-butyldimethylsilyloxy)acetaldehyde with a range of nitroolefins, followed by an intermolecular aza-Henry reaction with imine, provided iminosugar derivatives with five contiguous stereocenters in very high enantiomeric excess in one pot. The stereochemistry of the aza-Henry reaction was substrate controlled and is explained by a six-membered cyclic transition-state model.
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