Science of Synthesis

Marsden, S. P., Science of Synthesis, (2005) 26, 1050.

Acylation of organometallic reagents is an efficient and convergent approach to the synthesis of enones. Conceptually this may be achieved by the addition of an alkenylmetal to an acyl donor, or addition of an organometallic to an α,β-unsaturated acyl donor. In the latter case, appropriate choice of reagents and conditions to ensure clean 1,2-addition rather than 1,4-addition is essential. Additionally, since the product enones themselves can function as electrophiles (in either 1,2- or 1,4-addition mode), care must be taken in both reaction modes to select reaction conditions where such competitive reactions are minimized.