Selective reduction of α,β-epoxyketones to β-hydroxyketones using silyllithium reagents

2,3-Epoxy-1-phenyl-1-propanone was reduced to 3-hydroxy-1-phenyl-1-propanone using dimethylphenyl-, methyldiphenyl- or triphenylsilyllithium in THF at −40 °C. The methyldiphenylsilyllithium reagent was superior, providing the product in 70% yield. The reaction is believed to proceed via an epoxide ring-opening assisted Brook rearrangement. A number of α,β-epoxyketones underwent reduction with methyldiphenylsilyllithium to form the corresponding β-hydroxyketones in moderate to good yield.