First enantioselective reductive amination of α-fluoroenones

Guillaume Dutheuil (1) , Laëtitia Bailly (1) , Samuel Couve-Bonnaire (1) , Xavier Pannecoucke (1)

1 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse

From α-fluoroenones 2, a synthesis of (E) ketone oxime O-alkyl ethers 5 is reported with good to excellent yields. Then the first enantioselective reduction of these ketimines, via oxazaborolidine, is described with moderate to good enantiomeric excesses, leading to valuable chiral fluoroallylic amines 1.

Domains: Chemical Sciences

Guillaume Dutheuil, Laëtitia Bailly, Samuel Couve-Bonnaire, Xavier Pannecoucke. First enantioselective reductive amination of α-fluoroenones. Journal of Fluorine Chemistry, 2007, 128 (1), pp.34-39. ⟨10.1016/j.jfluchem.2006.09.013⟩. ⟨hal-02378329⟩