First enantioselective reductive amination of α-fluoroenones

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.

Graphical abstractThe first enantioselective reduction of ketimines, via oxazaborolidine, is described with moderate to good enantiomeric excesses, leading to valuable chiral fluoroallylic amines 1. Figure optionsDownload full-size imageDownload as PowerPoint slide