Ceric Ammonium Nitrate Catalyzed aza-Michael Addition of Aliphatic Amines to (alpha),(beta)-Unsaturated Carbonyl Compounds and Nitriles in Water

Ceric ammonium nitrate (3 mol%) efficiently catalyzes the aza-Michael reaction of amines with (alpha),(beta)-unsaturated carbonyl compounds in water to produce the corresponding (beta)-amino carbonyl compounds in good to excellent yields (55-99%) for most of the compounds under mild conditions. The reaction is procedurally simple and displays limited chemoselectivity, as aromatic amines were found to be unreactive.