A new efficient synthesis of α-methyl-β-ketoesters through an Eschenmoser sulfide reaction

Various α-methyl-β-ketoesters were readily synthesized through Eschenmoser condensation of thioamides with a commercially available bromoester. β-Enaminoesters were easily prepared through this sulfide contraction reaction and were hydrolysed to afford the corresponding β-ketoesters in moderate to g...

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Bibliographic Details
Published inCanadian journal of chemistry Vol. 82; no. 8; pp. 1289 - 1293
Main Authors Bellec, Christian, Gaurat, Olivier
Format Journal Article
LanguageEnglish
Published Ottawa, Canada NRC Research Press 01.08.2004
Natl Research Council Canada
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
ACID
1,3-DIKETONES
ALKYLATION
AMINO ESTERS
CONVENIENT
SULFUR
beta-enaminoesters
alpha-alkylated-beta-ketoesters
Eschenmoser
KETO-ESTERS
CONTRACTION
DERIVATIVES
ALKALOIDS
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Summary:Various α-methyl-β-ketoesters were readily synthesized through Eschenmoser condensation of thioamides with a commercially available bromoester. β-Enaminoesters were easily prepared through this sulfide contraction reaction and were hydrolysed to afford the corresponding β-ketoesters in moderate to good yields.Key words: α-alkylated-β-ketoesters, Eschenmoser, β-enaminoesters.
ISSN:0008-4042
1480-3291
DOI:10.1139/v04-088