Nickel-catalysed conjugate addition to trimethylaluminum to sterically hindered α,β-unsaturated ketones

Article abstract of DOI:10.1055/s-1995-3901

Nickel acetylacetonate is an efficient catalyst for the 1,4-addition of trimethylaluminum to α,β-unsaturated ketones. The reaction is strongly solvent dependent and gives best results in tetrahydrofuran or ethyl acetate. The reaction is especially useful for the nucleophilic 1,4-methyl transfer to sterically hindered enones. A β-cuparenone synthesis via conjugate methyl group addition to an enone precursor is described.