title: Combining asymmetric catalysis with natural product functionalization through enantioselective alpha-fluorination.
abstract: An examination into the derivatization of various natural products using newly developed alpha-fluorination methodology is disclosed. An activated ketene enolate, generated from an acid chloride, is allowed to react with an electrophilic fluorine source (NFSi). Quenching the reaction with a nucleophilic natural product produces biologically relevant alpha-fluorinated carbonyl derivatives of select chemotherapeutics, antibiotics, and other pharmaceuticals.
authors.affiliation: Department of Chemistry, Johns Hopkins University, 3400 North Charles Street, Baltimore, Maryland 21218, USA.
authors.forename: Jeremy
authors.initials: J
authors.lastname: Erb
authors.forename: Ethan
authors.initials: E
authors.lastname: Alden-Danforth
authors.forename: Nathan
authors.initials: N
authors.lastname: Kopf
authors.forename: Michael T
authors.initials: MT
authors.lastname: Scerba
authors.forename: Thomas
authors.initials: T
authors.lastname: Lectka
mesh_terms: D001688:Biological Products / Q000737:chemistry*; D002384:Catalysis; D005461:Fluorine / Q000737:chemistry*; D054879:Halogenation; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D007659:Ketones; D005461:Fluorine