Pd(0)-catalyzed conjugate addition of benzylzinc chlorides to alpha,beta-enones in an atmosphere of carbon monoxide: preparation of 1,4-diketones.
Pd(0)-catalyzed conjugate addition of benzylzinc chloride to methyl vinyl ketone in the presence of chlorotrimethylsilane and lithium chloride in an atmosphere of carbon monoxide at room temperature afforded 1-phenyl-2,5-hexanedione monosilyl enol ether. In this catalytic carbonylation, four components are connected in one reaction. Successive acidic workup generated a variety of 1,4-diketones from substituted benzylzinc chlorides or related compounds and alpha,beta-enones. Some products were converted to cyclopentenones or five-membered heterocyclic compounds containing an N, O, or S atom.
Yuguchi
Motoki
M
Laboratory of Organic Synthesis, Division of Molecular Chemistry Graduate School of Engineering, Hokkaido University, Sapporo 060-8628, Japan.
Tokuda
Masao
M
Orito
Kazuhiko
K