Stereoselective Synthesis of β-Amino Ketones: A Three-Component Mannich-Type Reaction of Aromatic Aldehydes, Anilines, and Cyclohexanone Using Amberlyst-15

Abstract

A three-component Mannich-type reaction of aromatic aldehydes, anilines, and cyclohexanone in the presence of Amberlyst-15 affords the corresponding β-amino ketones in good yields at room temperature. The conversion is highly diastereoselective, favoring the formation of anti-isomers.

Keywords:

• Amberlyst-15
• β-amino ketone
• Mannich-type reaction
• stereoselective synthesis
• three-component reaction

ACKNOWLEDGMENTS

The authors thank the Council of Scientific and Industrial Research and the University Grants Commission, New Delhi, for financial assistance.

Notes

^a The structures of the products were determined from their ¹H NMR and MS data.

^b The ratio of syn and anti was determined from the ¹H NMR spectra of the crude products.

Part 175 in the series “Studies on Novel Methodologies.”