Combining asymmetric catalysis with natural product functionalization through enantioselective alpha-fluorination.
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.
Erb
Jeremy
J
Department of Chemistry, Johns Hopkins University, 3400 North Charles Street, Baltimore, Maryland 21218, USA.
Alden-Danforth
Ethan
E
Kopf
Nathan
N
Scerba
Michael T
MT
Lectka
Thomas
T
D001688:Biological Products / Q000737:chemistry*; D002384:Catalysis; D005461:Fluorine / Q000737:chemistry*; D054879:Halogenation; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D001688:Biological Products; D007659:Ketones; D005461:Fluorine