Stereocontrolled Iodolactonization of Erythro and Threo Tertiary Amides

Authors

David Rotella, Montclair State UniversityFollow
Xun Li, Université Laval

Document Type

Article

Publication Date

7-1-1990

Journal / Book Title

Heterocycles

Abstract

A series of α-mono and dialkyl-β-oxygenated (hydroxyl and alkyl ester) tertiary amides were subjected to iodolactonization and it was observed that with only 1 exception, (threo11b), 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 α to the amide, iodolactonization is a viable strategy for the stereocontrolled preparation of highly substituted γ-butyrolactones.

Comments

This article is Open Access via CLOCKSS.

DOI

10.3987/COM-90-5389

Montclair State University Digital Commons Citation

Rotella, David and Li, Xun, "Stereocontrolled Iodolactonization of Erythro and Threo Tertiary Amides" (1990). Department of Chemistry and Biochemistry Faculty Scholarship and Creative Works. 51.
https://digitalcommons.montclair.edu/chem-biochem-facpubs/51

Published Citation

Rotella, D., & Li, X. (1990). Stereocontrolled iodolactonization of erythro and threo tertiary amides. Heterocycles, 31(7), 1205-1211.