Abstract
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
Substances
-
Amines
-
Cinchona Alkaloids
-
Hydrocarbons, Fluorinated
-
Ketones