Organocatalytic Asymmetric Halogenation/Semipinacol Rearrangement: Highly Efficient Synthesis of Chiral alpha-Oxa-Quaternary beta-Haloketones

  • Chen Z
  • Zhang Q
  • Chen Z
 et al. 
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A novel asymmetric halogenation/semipinacol rearrangement reaction catalyzed by cinchona alkaloid derivatives was developed. Two types of beta-haloketones (X = Br, Cl) were obtained with up to 95% yield and 99% enantiomeric excess. The desired (+) and (-) enantiomers of the beta-haloketones were readily obtained.

Author-supplied keywords

  • aldehydes
  • allylic alcohols
  • bromolactonization
  • bronsted acid
  • complex
  • enantioselective halocyclization
  • hydroxy epoxides
  • iodolactonization
  • modified cinchona alkaloids
  • semipinacol rearrangement

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  • Z M Chen

  • Q W Zhang

  • Z H Chen

  • H Li

  • Y Q Tu

  • F M Zhang

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