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Synlett 1997; 1997(12): 1441-1443
DOI: 10.1055/s-1997-1057
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Synthesis of 2-Substituted Nitrogen Heterocycles Using para-Toluenesulfonyl Iodide in a Key Step

D. C. Craig, G. L. Edwards* , C. A. Muldoon
  • *School of Chemistry, University of New South Wales, Sydney, N.S.W., 2052, Australia, FAX: (+)61 2 9385 6141; E-mail: g.edwards@unsw.edu.au
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Publication History

Publication Date:
31 December 2000 (online)

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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.

free radicals - sulfones - pyrrolidines - piperidines - diastereoselectivity