Iridium-catalyzed aziridination of aliphatic aldehydes, aliphatic amines and ethyl diazoacetate

Abstract

Three-component coupling reactions of aliphatic aldehydes, aliphatic amines and ethyl diazoacetate to the corresponding aziridine derivatives has been achieved by the use of [Ir(cod)Cl]₂ as a catalyst under mild conditions; for instance, the reaction of n-butyraldehyde, tert-butylamine and ethyl diazoacetate in the presence of a catalytic amount of [Ir(cod)Cl]₂ in THF at −10 °C gave 1-tert-butyl-2-ethoxycarbonyl-3-propylaziridine in 85% yield in high stereoselectivity (cis : trans = 96∶4).