A Conjugate Addition-Elimination Route to Alkenoyltrimethylsilanes

Article abstract of DOI:10.1016/0040-4020(95)00561-L

Monosubstitution of 3,3-dichloro-1-(trimethylsilyl)-2-propenone (1) with organocuprates stereoselectively affords E-3-alkyl- and Z-3-phenyl-3-chloro-1-(trimethylsilyl)-2-propenones.Further substitution proceeds stereoselectively as a function of extant and incoming substituents. 1 was also reduced to E-3-chloro-1-(trimethylsilyl)-2-propenone and the latter converted to E-3-alkyl- and E-3-phenyl-1-(trimethylsilyl)-2-propenones.