Stereocontrolled iodolactonization of erythro and threo tertiary amides

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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 languageEnglish
Pages (from-to)1205-1211
Number of pages7
JournalHeterocycles
Volume31
Issue number7
StatePublished - 1 Jul 1990

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Amides
Hydroxyl Radical
Esters
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title = "Stereocontrolled iodolactonization of erythro and threo tertiary amides",
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.",
author = "David Rotella and Xun Li",
year = "1990",
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Stereocontrolled iodolactonization of erythro and threo tertiary amides. / Rotella, David; Li, Xun.

In: Heterocycles, Vol. 31, No. 7, 01.07.1990, p. 1205-1211.

Research output: Contribution to journalArticle

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T1 - Stereocontrolled iodolactonization of erythro and threo tertiary amides

AU - Rotella, David

AU - Li, Xun

PY - 1990/7/1

Y1 - 1990/7/1

N2 - 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.

AB - 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.

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