REGIO- AND STEREOSELECTIVITY IN THE ADDITION OF METAL N,N-DIMETHYLPHENYLACETAMIDE ENOLATES TO SOME CONJUGATED CARBONYL COMPOUNDS

Article abstract of DOI:10.1016/S0040-4020(01)82085-8

The nucleophilic addition of lithium, sodium, potassium and bromomagnesium N,N-dimethylphenylacetamide enolates to cinnamic aldehyde, chalcone and methyl cinnamate is studied.The regioselectivity of the reaction is found to depend on the metal counterion and other reaction conditions.The stereoselectivity under kinetic and thermodynamic conditions does not depend on the metal.The reactivity of the amide-enolates is compared with the reactivity of other enolates already studied.