Stereocontrolled Iodolactonization of Erythro and Threo Tertiary Amides
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.
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
Comments
This article is Open Access via CLOCKSS.