Highly stereoselective direct aldol reaction of 4-formylcoumarins with acetone catalyzed by L-proline in water–acetone mixtures

ABSTRACT

Organocatalyzed direct intermolecular aldol reactions have been developed for substituted 4-formylcoumarins with acetone in water using L-proline and phthalimido-prolinamide catalysts without use of additives. Stereoselective products obtained were in excellent yields (up to 97%) with high purity (up to 99%) and enatioselectivities (up to 95%). The isolated compounds were confirmed by infrared, NMR, high-performance liquid chromatography, and mass spectrometry and some of them by single-crystal x-ray crystallography.

GRAPHICAL ABSTRACT

KEYWORDS:

• Acetone
• aldol reaction
• 4-formylcoumarin
• phthalimido-prolinamide
• recyclable organocatalyst L-proline