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. © 2007 Elsevier Ltd. All rights reserved.
Mendeley saves you time finding and organizing research
Choose a citation style from the tabs below