Highly efficient regioselective ring openings of N-tosylaziridines to haloamines using ferric (III) halides

FeX3 (X = Cl, Br) were found to be very effective reagents and powerful catalysts for regioselective ring openings of a variety of N-tosylaziridines with them to afford the corresponding β-haloamines in good to excellent yields with high regioselectivity under mild conditions. At the same time, 13 new compounds were obtained firstly. Moreover, the β-bromoamine prepared could be transferred into β-nitroamine with NaNO2 in moderate yield.

Graphical abstractFeX3 (X = Cl, Br) were effective reagents for regioselective ring openings of various N-tosylaziridines with them to afford the β-haloamines in good to excellent yields and with high regioselectivity, and the β-haloamines obtained can be easily transferred into nitro compounds through the nucleophilic substitution to the Br with NaNO2.Figure optionsDownload full-size imageDownload as PowerPoint slide