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Communication | Special issue | Vol 64, No. 1, 2004, pp.45-50
Published online, 17th September, 2004
DOI: 10.3987/COM-04-S(P)26
Iodine-induced Cyclizations of N-Alkoxyaminoalkenes. A Stereocontrolled Approach to trans-2,6-Disubstituted Piperidine Alkaloids

David R. Williams,* Martin H. Osterhout, and George S. Amato

*Department of Chemistry, Indiana University, 800 E. Kirkwood Avenue, Bloomington, IN 47405-7102, U.S.A.

Abstract

Iodine-induced intramolecular cyclizations of γ-alkenyl-N-alkoxyamines preferentially produce 2,6-trans-disubstituted piperidines. Subsequent iodoetherifications of N-benzyloxypiperidines demonstrate the stereoselective transfer of oxygen to a proximate carbon via formation of bicyclic 1,3-syn-isoxazolidines. The strategy facilitates preparation of nonracemic piperidine diols from acyclic, optically active alcohols.