Synthesis of 4-Iodo-3-furanones Utilizing Electrophile-Induced Tandem Cyclization/1,2-Migration Reactions

Synthesis of 4-Iodo-3-furanones Utilizing Electrophile-Induced Tandem Cyclization/1,2-Migration Reactions

Two protocols for the construction of 4-iodo-3-furanones through a sequence consisting of cyclization and 1,2-migration of 2-alkynyl-2-silyloxy carbonyl compounds were developed. In one, electrophilic cyclization is directly induced by N-iodosuccinimide (NIS). In the second less limited variant, AuC...

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Veröffentlicht in:Journal of organic chemistry 2007-07, Vol.72 (14), p.5435-5438
Hauptverfasser: Crone, Benedikt, Kirsch, Stefan F
Format: Artikel
Sprache:eng
Schlagworte:
Alkylation
Chemistry
Cyclization
Electrons
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Iodine - chemistry
Lactones - chemical synthesis
Lactones - chemistry
Molecular Structure
Organic chemistry
Preparations and properties
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Zusammenfassung:Two protocols for the construction of 4-iodo-3-furanones through a sequence consisting of cyclization and 1,2-migration of 2-alkynyl-2-silyloxy carbonyl compounds were developed. In one, electrophilic cyclization is directly induced by N-iodosuccinimide (NIS). In the second less limited variant, AuCl3 catalyzes the tandem reaction in the presence of NIS to provide highly substituted heterocycles in moderate to excellent yields.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo070695n