Aza-Henry Reaction with CF3-Ketimines: An Efficient Approach to Trifluoromethylated β-Nitroamines, 1,2-Diamines, α-­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 β-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 β-nitroamines bearing CF3 group was developed. α-CF3-β-nitroamines can easily be converted into trifluoromethylated 1,2-diamines, α-aminooximes, and imidazolidinones. [ABSTRACT FROM AUTHOR]