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  • Title: N-heterocyclic carbene catalyzed enantioselective α-fluorination of aliphatic aldehydes and α-chloro aldehydes: synthesis of α-fluoro esters, amides, and thioesters.
    Author: Dong X, Yang W, Hu W, Sun J.
    Journal: Angew Chem Int Ed Engl; 2015 Jan 07; 54(2):660-3. PubMed ID: 25394812.
    Abstract:
    The asymmetric fluorination of azolium enolates that are generated from readily available simple aliphatic aldehydes or α-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 α-fluoro esters, amides, and thioesters with excellent enantioselectivity. Pyrazole was identified as an excellent acyl transfer reagent for catalytic amide formation.
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