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Authors: .
DOI: http://dx.doi.org/10.24193/subbchem.2017.1.16
Published Online: 2017-03-17
Published Print: 2017-03-31
VIEW PDF: SYNTHESIS OF THREE NEW BIFUNCTIONAL GLUCOSE-THIOUREA ORGANOCATALYSTS AND THEIR APPLICATION IN ASYMMETRIC MICHAEL ADDITION
Three new glucose-based asymmetric bifunctional organocatalysts containing a 6-aminopyridyl or a 6-methylpyridyl or a cinchona unit were synthesized. Asymmetric Michael addition of pentane-2,4-dione to β-nitrostyrene was catalyzed successfully by these catalysts. In case of the cinchona based glucose-thiourea derivate the S enantiomer of the corresponding Michael adduct was formed with moderate enantiomeric excess in three different solvents.
Keywords: organocatalyst, carbohydrates, cinchona alkaloids, Michael addition, asymmetric syntheses
