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1.1.5.3.1.2 α-Fluorination of Ketones

DOI: 10.1055/sos-SD-204-00082

Mukherjee, S.Science of Synthesis: Asymmetric Organocatalysis, (20121236.

The successful enamine-catalyzed asymmetric α-fluorination of aldehydes could not be implemented for ketone substrates except in one report on chiral secondary amine catalyzed α-fluorination of cyclohexanone, which met with very limited success.[‌31‌] Relatively slow enamine formation from ketones with secondary amines and lower conformational rigidity of ketone-derived enamines are believed to be the reasons for the failure of chiral secondary amines to effect α-fluorination of ketones with useful levels of enantioselectivity.

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