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.
| Original language | English |
|---|---|
| Pages (from-to) | 1205-1211 |
| Number of pages | 7 |
| Journal | Heterocycles |
| Volume | 31 |
| Issue number | 7 |
| DOIs | |
| State | Published - 1 Jul 1990 |