How cinchona alkaloid-derived primary amines control asymmetric electrophilic fluorination of cyclic ketones

J Am Chem Soc. 2014 Jul 9;136(27):9556-9. doi: 10.1021/ja504714m. Epub 2014 Jun 26.


The origin of selectivity in the α-fluorination of cyclic ketones catalyzed by cinchona alkaloid-derived primary amines is determined with density functional calculations. The chair preference of a seven-membered ring at the fluorine transfer transition state is key in determining the sense and level of enantiofacial selectivity.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Amines / chemistry*
  • Cinchona Alkaloids / chemistry*
  • Halogenation
  • Hydrocarbons, Fluorinated / chemical synthesis*
  • Hydrocarbons, Fluorinated / chemistry
  • Ketones / chemistry*
  • Molecular Structure
  • Quantum Theory


  • Amines
  • Cinchona Alkaloids
  • Hydrocarbons, Fluorinated
  • Ketones