Enantioselective ring opening of epoxides by fluoride anion promoted by a cooperative dual-catalyst system

J Am Chem Soc. 2010 Mar 17;132(10):3268-9. doi: 10.1021/ja100161d.


An enantioselective method for the synthesis of beta-fluoroalcohols by catalytic nucleophilic fluorination of epoxides is described. Mild reaction conditions and high selectivity are made possible by the use of benzoyl fluoride as a soluble, latent source of fluoride anion. A chiral amine and chiral Lewis acid serve as cooperative catalysts for desymmetrizations of five- through eight-membered cyclic epoxides, affording products in up to 95% ee. The cocatalytic protocol is also effective for kinetic resolutions of racemic terminal epoxides, which proceed with k(rel) values as high as 300.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Alcohols / chemical synthesis*
  • Anions / chemistry
  • Catalysis
  • Cyclization
  • Epoxy Compounds / chemistry*
  • Fluorides / chemistry*
  • Hydrocarbons, Cyclic / chemistry
  • Hydrocarbons, Fluorinated / chemical synthesis*
  • Kinetics
  • Stereoisomerism


  • Alcohols
  • Anions
  • Epoxy Compounds
  • Hydrocarbons, Cyclic
  • Hydrocarbons, Fluorinated
  • Fluorides