Highly Efficient Asymmetric Mannich Reaction of Dialkyl α-Diazomethylphosphonates with N-Carbamoyl Imines Catalyzed by Chiral Bronsted Acids

An efficient method involving the first use of chiral phosphoric acids as catalysts in the asymmetric Mannich reaction oil dialkyl diazomethylphosphonates and N-carbamoyl imines is developed. With only 0.1 mol % catalyst 1f, the reaction proceeded smoothly and produced the corresponding beta-amino-alpha-diazophosphonate with up to 97% yield and >99% ee.