Direct Synthesis of N-Unprotected Aziridines from Olefins Using a Rhodium Catalyst

Falck et al. have reported the direct synthesis of N-unprotected aziridines from olefins. According to their results, various olefins can be converted into the corresponding N-unsubstituted aziridines in high yields and stereospecifically by the treatment of a hydroxylamine (1) and a catalytic amount of Rh₂(esp)₂. Conventionally, aziridinations of olefins require amines having an electron-withdrawing protecting group and in some cases side reactions occur. To obtain the N-free aziridines, a sequential deprotection is performed. Aziridine moieties can be found in natural products such as azinomycins and can be regarded as significant building blocks. Thus, this reaction is expected to be applied for the direct synthesis of the N-unsubstituted aziridines from olefins.