Combining asymmetric catalysis with natural product functionalization through enantioselective alpha-fluorination.

Research paper by Jeremy J Erb, Ethan E Alden-Danforth, Nathan N Kopf, Michael T MT Scerba, Thomas T Lectka

Indexed on: 31 Dec '09Published on: 31 Dec '09Published in: Journal of Organic Chemistry


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.