Reactions of α,β-unsaturated ketones with arylacetonitriles

Abstract

1,3-Diaryl-2-propene-1-ones I react with arylacetonitriles II in the presence of sodium ethoxide at room temperature to give a single diastereomer of the corresponding 2,3-diaryl-4-aroylbutyronitriles III. The structures of the reaction products were established by infrared, nuclear magnetic resonance, and mass spectral data as well as elemental analysis. The diastereomeric purity was determined by NMR measurements using lanthanide shift reagents. The observed resonances did not show any resolved diastereomeric proton signals.