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

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 (u...

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Bibliographic Details
Published in:Synthetic communications 2016-08, Vol.46 (16), p.1386-1395
Main Authors: Holiyachi, Megharaja, Shastri, Samundeeswari L., Chougala, Bahubali M., Shastri, Lokesh A., Sunagar, Vinay A.
Format: Article
Language:English
Subjects:
4-formylcoumarin
Acetone
aldol reaction
phthalimido-prolinamide
recyclable organocatalyst L-proline
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Summary: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.
ISSN:0039-7911
1532-2432
DOI:10.1080/00397911.2016.1205197