A new tandem synthesis of bis(β,β′-dialkoxy carbonyl) compounds by oxidative cleavage of aziridines under metal-free conditions

Abstract

An efficient and new approach has been developed to synthesize bis(β,β′-dialkoxy carbonyl) derivatives through the reaction between N-tosylaziridines and malonate esters under ambient air using ^tBuOK in DMSO solvent. A plausible reaction pathway has been predicted. Control experiments suggested that the reactions proceed through the formation of α-aminoketones. This reaction offers a broad substrate scope, metal-free synthesis, excellent regioselectivity, easily accessible reactants, and simple operation. A gram-scale synthesis demonstrates the potential applications of the present method.