Synthesis of 2-substituted nitrogen heterocycles using para-toluenesulfonyl iodide in a key step

Article abstract of DOI:10.1055/s-1997-1057

N-Protected aminoalkenes undergo radical addition of tosyl iodide to give β-iodosulfones which can subsequently be induced to cyclise giving 2-substituted pyrrolidines and piperidines. Incorporation of an α-methylbenzyl group at nitrogen leads to a diastereoselective ring closure where the constituent diastereoisomers can be separated readily giving chiral, non-racemic heterocycles.