Low Catalyst Loading, Highly Efficient D-glucosamine-derived Organocatalysts for Asymmetric Aldol Reactions
Glucosamine as a kind of important nature chiral scaffold is widely regarded for its obvious advantages
such as cheap, stable and readily available. In this communication, we reported the introduction of
L-proline group at the amino functional group of D-glucosamine resulted in several efficient prolinamide organocatalysts,
which could efficiently catalyze the asymmetric aldol reaction between acetone and various
substituted benzaldehydes in the neat condition. Under the optimized conditions, 0.5 mol% of organocatalyst
gave excellent chiral selectivity (83% ee value) with 88% yield, which was higher than that obtained using 10 mol% of organocatalyst.
Keywords: Aldol reaction, asymmetric catalysis, carbohydrate, organocatalyst.
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