1,2-Migration of the Thio Group in Allenyl Sulfides: Efficient Synthesis of 3-Thio-Substituted Furans and Pyrroles

The copper‐catalyzed cycloisomerization of thioalkynyl ketones 1 a and thioalkynyl imines 1 b allows the efficient synthesis of 3‐thio‐substituted furans 3 a and pyrroles 3 b, an important class of heterocyclic unit previously inaccessible by standard cycloisomerization techniques. A plausible mecha...

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Published inAngewandte Chemie (International ed.) Vol. 42; no. 1; pp. 98 - 101
Main Authors Kim, Joseph T., Kel'in, Alexander V., Gevorgyan, Vladimir
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 03.01.2003
WILEY‐VCH Verlag
Wiley
Subjects
Catalysis
Chemistry
Chemistry, Multidisciplinary
Copper - chemistry
Cyclization
Furans - chemical synthesis
Furans - chemistry
heterocycles
homogeneous catalysis
Molecular Structure
Nitrogen - chemistry
nitrogen heterocycles
Physical Sciences
Pyrroles - chemical synthesis
Pyrroles - chemistry
Science & Technology
Sulfhydryl Compounds - chemistry
Sulfides - chemistry
sulfur
MIGRATION
homogeneous catalysis
heterocycles
nitrogen heterocycles
sulfur
IONS
cyclization
STEREOSELECTIVE SYNTHESIS
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Summary:The copper‐catalyzed cycloisomerization of thioalkynyl ketones 1 a and thioalkynyl imines 1 b allows the efficient synthesis of 3‐thio‐substituted furans 3 a and pyrroles 3 b, an important class of heterocyclic unit previously inaccessible by standard cycloisomerization techniques. A plausible mechanism for this unusual cascade involves a 1,2‐migration of the thio group in the intermediate keto‐ and iminoallenyl sulfides 2. DMA=N,N‐dimethylacetamide.
Bibliography:istex:CD4DB7482C0589C5E4DBFB8D1284D3BB120F86C9
The support of the National Science Foundation (CHE-0096889) and the National Institutes of Health (GM-64444) is gratefully acknowledged.
ArticleID:ANIE200390064
ark:/67375/WNG-29W1P5VW-8
The support of the National Science Foundation (CHE‐0096889) and the National Institutes of Health (GM‐64444) is gratefully acknowledged.
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200390064