Three step synthesis of single diastereoisomers of the vicinal trifluoro motif

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Abstract

A three step route to single diastereoisomers of the vicinal trifluoromethyl motif is described. The route starts from either syn- or anti-alpha,beta-epoxy alcohols and takes a direct approach in that each of the three steps introduces a fluorine atom in a regio- and stereospecific manner. Starting from either the syn- or the anti-alpha,beta-epoxy alcohol, stereospecific reactions generate two separate diastereoisomeric series of this motif. The route is a significant improvement on an earlier six step strategy.

Original languageEnglish
Article number61
Number of pages9
JournalBeilstein Journal of Organic Chemistry
Volume5
DOIs
Publication statusPublished - 5 Nov 2009

Keywords

  • C-F bond
  • organo-fluorine chemistry
  • stereospecific fluorination
  • vicinal trifluoro motif
  • Kinetic resolution
  • Hydrogen-fluoride
  • Fluorination
  • Chemistry
  • Epoxides
  • Bond

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