Asymmetric Synthesis of Trisubstituted Aziridines via Aza-Darzens Reaction of Chiral Sulfinimines

Abstract

The aza-Darzens reaction of substituted 2-bromoesters with chiral tert-butane- and mesitylsulfinimines provides a rapid access to a range of highly substituted aziridines in good yields and excellent levels of stereoselectivity. The synthetic potential of this protocol is further enhanced by the successful removal of the sulfinyl motif, yielding simple access to chiral N-H aziridines in just three steps from commercial aldehyde precursors.