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

  • Reynolds S
  • Wengryniuk S
  • Hartel A
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Abstract

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.

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Authors

  • Samantha C. Reynolds

  • Sarah E. Wengryniuk

  • Aaron M. Hartel

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