Decarboxylative Amination of SMAHOs by Dialkyl Azodicarboxylates

The organocatalyzed decarboxylative addition of substituted malonic acid half oxyesters (SMAHOs) to dialkyl azodicarboxylates led to the formation of α-aminoester derivatives. The reaction can be performed under mild reaction conditions using 1,4-diazabicyclo[2.2.2]octane (DABCO) as a catalyst and displayed a rather important scope.

Abstract

The decarboxylative addition of substituted malonic acid half oxyesters (SMAHOs) to dialkyl azodicarboxylates is described. The reaction was promoted by 1,4-diazabicyclo[2.2.2]octane (DABCO) as an organocatalyst in heated toluene. High yields of the coupling products were generally obtained, and the scope of the reaction proved rather important with the potential presence of functionalized side chains at the α-position, affording an original access to α-aminoester derivatives.