Yield and selectivity enhancement by trimethylsilyl chloride in the conjugate addition of stabilized organolithiums

Article abstract of DOI:10.1016/0040-4039(95)01919-9

The yield and selectivity in the conjugate addition of some stabilized organolithiums to α,β-unsaturated carbonyl compounds, especially easily polymerized ones, are increased in the presence of trimethylsilyl chloride, alone or in combination with hexamethylphosphoric triamide. E-silyl enol ethers bearing the versatile phenylthio group are obtained prior to hydrolysis. Some synthetic uses are demonstrated.