Diastereoselective synthesis of aziridine esters via amino selanyl esters

Abstract

A synthesis of aziridine esters based on the cyclisation of amino selanyl esters induced by the selanyl group activation was developed with either the Meerwein salt or NBS. Two asymmetric approaches are proposed: the diastereoselective reductions of α-selanyl β-iminoesters derived from α-oxoesters, which lead to cis chiral aziridine esters 6 and 6′ ; and the diastereoselective conjugate additions of a chiral amide to α,β-unsaturated esters providing trans chiral aziridine esters 6 and 6″ .