Expedient syntheses of β-iodofurans by 5-endo-dig cyclisations

Sean P. Bew, Gamila M. M. El-Taeb, Simon Jones, David W. Knight, Wen-Fei Tan

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55 Citations (Scopus)

Abstract

5-endo-dig cyclisations of 3-alkyne-1,2-diols using iodine as the electrophile proceed smoothly to deliver excellent yields of the corresponding β-iodofurans. The necessary precursors are available from a number of different approaches, notably regioselective bis-hydroxylation of conjugated enynes and the addition of acetylides to α-hydroxy carbonyl groups. The initial iodofurans can be homologated using a number of strategies, ranging from various transition metal-catalysed couplings to halogen-metal exchange and subsequent coupling with an electrophile. Hence, this method overall represents a flexible, relatively brief and very efficient approach to a variety of highly substituted furans. © Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
Original languageEnglish
Pages (from-to)5759-5770
Number of pages12
JournalEuropean Journal of Organic Chemistry
Volume2007
Issue number34
DOIs
Publication statusPublished - Dec 2007

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