Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact:

Price: ¥ 4,400 (Yen only)
Period: This Article can be accessed for 7 days.

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.


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.