Synthesis of β-aminovinylphosphonates by organocatalytic nucleophilic displacement of acetate with amines

Article abstract of DOI:10.1016/j.tetlet.2010.05.050

The synthesis of diethyl β-aminovinylphosphonates 2 from acetoxy phosphonate 1 is described. The reaction entails an organocatalyzed substitution of the acetoxy group by primary or secondary amines. The use of a catalytic amount of DABCO is necessary if the amine is not nucleophilic enough, otherwise a strong nucleophilic amine can react without organocatalyst. The reaction led to a series of functionalized title compounds in good to excellent yields.