Samarium(II)-iodide catalysed addition of N-chloroamines to double bonds, an iodide-catalysed reaction

N-Pentenyl-N-chloroamines react under virtually neutral conditions under samarium(II)-iodide catalysis to the corresponding piperidines. These conditions allow the complete rearrangement of 2-(chloromethylpyrrolidines), the proposed primary products of the reaction, via an aziridinium ion to the corresponding 3-chloro-piperidines. The reaction does not seem to proceed via free radicals, as a radical cascade cyclisation could not be observed. Therefore not the samarium(II), but the iodide seems to catalyze the reaction.