title: How cinchona alkaloid-derived primary amines control asymmetric electrophilic fluorination of cyclic ketones.
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.
authors: Department of Chemistry and Biochemistry, University of California, Los Angeles , 607 Charles E. Young Drive East, Los Angeles, California 90095-1569, United States.
authors: Yu-hong
authors: YH
authors: Lam
authors: K N
authors: KN
authors: Houk
mesh_terms: D000588:Amines / Q000737:chemistry*; D002930:Cinchona Alkaloids / Q000737:chemistry*; D054879:Halogenation; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D011789:Quantum Theory
chemical_list: D000588:Amines; D002930:Cinchona Alkaloids; D006845:Hydrocarbons, Fluorinated; D007659:Ketones