61. N. Jabri, A. Alexakis, J.F. Normant,
    “Palladium mediated synthesis of conjugate (E) or (Z) enones and unsymmetrical divinyl ketones. One-pot preparation of Isoegomaketone”
    Tetrahedron 1986, 42, 1369-1380.

The palladium (o) catalyzed coupling of acyl halides or anhydrides with alkenyl copper reagents furnishes α,β ethylenic ketones and α,β-α,β' diethylenic ketones in high yield. The substitution pattern of the alkenyl copper reagent, directly obtained by carbocupration of alkynes, is fully retained. Anhydrides of Z-ethylenic acids also retain their Z stereochemistry. β-halogeno-vinyl ketones react under the above conditions to afford α,β-γ,δ dienones. An efficient one-pot synthesis of Z or ε isoegomaketone is reported.

DOI : 10.1016/S0040-4020(01)87356-7 

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