STRICTLY REGIO-CONTROLLED METHOD FOR α-ALKENYLATION OF CYCLIC KETONES VIA PALLADIUM-CATALYZED CROSS COUPLING

Article abstract of DOI:10.1016/0040-4039(91)80010-4

Cyclic α-iodoenones and α-triflyloxyenones, but not α-bromoenones, smoothly react with alkenylzinc and related derivatives in the presence of a catalytic amount of a palladium-phosphine complex, such as Pd(PPh3)4 or Cl2Pd(PPh3)2 treated with n-BuLi (2 equiv), to give α-alkenylenones which can be conjugatively reduced to the corresponding α-alkenyl ketones with complete retention of both enone regiochemistry and alkenyl stereochemistry.