N-Heterocyclic Carbene Catalyzed Enantioselective alpha-Fluorination of Aliphatic Aldehydes and alpha-Chloro Aldehydes: Synthesis of alpha-Fluoro Esters, Amides, and Thioesters

摘要

The asymmetric fluorination of azolium enolates that are generated from readily available simple aliphatic aldehydes or -chloro aldehydes and N-heterocyclic carbenes (NHCs) is described. The process significantly expands the synthetic utility of NHC-catalyzed fluorination and provides facile access to a wide range of -fluoro esters, amides, and thioesters with excellent enantioselectivity. Pyrazole was identified as an excellent acyl transfer reagent for catalytic amide formation.