Stereocontrolled Iodolactonization of Erythro and Threo Tertiary Amides
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.
MSU 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.