A straightforward and highly diastereoselective access to functionalized monofluorinated cyclopropanes via a Michael initiated ring closure reaction

Org Lett. 2013 Nov 1;15(21):5598-601. doi: 10.1021/ol402837u. Epub 2013 Oct 18.


The synthesis of highly functionalized monofluorinated cyclopropanes based on a Michael Initiated Ring Closure (MIRC) reaction has been developed. The addition of quaternary ammonium salts derived from ethyl bromofluoroacetate on a panel of electron deficient alkenes followed by cyclization gave rise to an efficient access to monofluorinated cyclopropanes with good yields and remarkable diastereoselectivity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry
  • Ammonium Compounds / chemistry
  • Catalysis
  • Cyclopropanes / chemical synthesis*
  • Cyclopropanes / chemistry*
  • Hydrocarbons, Fluorinated / chemical synthesis*
  • Hydrocarbons, Fluorinated / chemistry*
  • Molecular Structure
  • Stereoisomerism


  • Alkenes
  • Ammonium Compounds
  • Cyclopropanes
  • Hydrocarbons, Fluorinated