Alkylation of nonstabilized aziridinylmagnesiums catalyzed by Cu(I) iodide: a new synthesis of amines, including optically active form, bearing a quaternary chiral center

Abstract

A high-yield alkylation of aziridinylmagnesiums, which were generated from sulfinylaziridines with EtMgBr by sulfoxide–magnesium exchange, with primary alkyl halides in the presence of Cu(I) iodide as a catalyst, was realized. The alkylated aziridines were converted in quantitative yield to amines bearing a quaternary chiral center by hydrogenation with Pd(OH) 2. A synthesis of the optically active amines, bearing a quaternary chiral center, was realized, starting from optically active ( R)-chloromethyl p-tolyl sulfoxide, in good overall yield by the presented method.