The cinnamate-based aminohalogenation provides an easy access to antimethyl 3-aryl-N-p-tosyl- and N-o-nosyl-aziridine-2-carboxylates

Abstract

The first application of trans-alkyl cinnamate-based aminohalogenation to the synthesis of anti methyl 3-aryl-N-(p-toluene)sulfonylaziridine-2- carboxylates and anti methyl 3-aryl-N-(o-nitrobenzene)sulfonylaziridine-2- carboxylates was described. The synthesis was easily carried out by mixing alkyl cinnamate-derived haloamines with potassium carbonate in acetonitrile at room temperature. Good to excellent yields (83-97% for N-p-Ts and 75-94% for N-o-Ns trans-aziridine-2-carboxylates, respectively) have been achieved for 11 examples.