First enantioselective reductive amination of alpha-fluoroenones

From alpha-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. (c) 2006 Elsevier B.V. All rights reserved.