Stereocontrolled iodolactonization of erythro and threo tertiary amides

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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 languageEnglish
Pages (from-to)1205-1211
Number of pages7
Issue number7
StatePublished - 1 Jul 1990


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