Aza-Henry Reaction with CF3-Ketimines: An Efficient Approach to Trifluoromethylated [beta]-Nitroamines, 1,2-Diamines, [alpha]-­Aminooximes, and Imidazolidinones

CF3-Substituted ketimines synthesized from trifluoroacetone, hexafluoroacetone, and trifluoroacetophenones were studied in aza-Henry reactions with nitroalkanes. We found that nitromethane and nitropropane react with CF3-substituted ketimines to form the target [beta]-nitroamines in high yield. The aza-Henry reaction proceeded under mild conditions in the presence of an appropriate base. A new simple method for the synthesis of [beta]-nitroamines bearing CF3 group was developed. [alpha]-CF3-[beta]-nitroamines can easily be converted into trifluoromethylated 1,2-diamines, [alpha]-aminooximes, and imidazolidinones.