Palladium catalyzed reductive decarboxylation of allyl α-alkenyl- β-ketoesters. A new synthesis of (E)-3-alkenones

Article abstract of DOI:10.1016/j.tetlet.2005.11.122

The reductive decarboxylation of α-alkenyl derivatives of allyl-β-ketoesters was achieved by use of palladium(0) catalyst generated in situ from Pd(OAc)₂ and PPh₃, with triethylammonium formate as the hydride source, in THF. The reaction proceeds smoothly and cleanly, with linear alkenyl derivatives of allyl-β-ketoesters, to afford (E)-3-alkenones in good to excellent yields (73-92%) and high stereoselectivity (>98%).