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Communication | Regular issue | Vol 31, No. 7, 1990, pp.1205-1211
Published online, 1st January, 1970
DOI: 10.3987/COM-90-5389
Stereocontrolled Iodolactonization of erythro and threo Tertiary Amides

David P. Rotella* and Xun Li

*Department of Pharmacology, School of Pharmacy, University of Mississippi, University, Mississippi 38677, U.S.A.

Abstract

A series of α-amino and dialkyl-β-oxygenated (hydroxyl and alkyl ester) tertiary amides were subjected to iodolactonization and it was observed that with only 1 exception, (threo 11b), all of the compounds cyclized with useful levels of stereoselection (at least 3:1). While the origin of this effect is obscure, these results suggest that in such amide substrates with at least one substituent larger than methyl a to the amide, iodolactonization is a viable strategy for the stereocontrolled preparation of highly substituted γ-butyrolactones.