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

Bew, Sean P. ORCID: https://orcid.org/0000-0002-9087-9463, El-Taeb, Gamila M. M., Jones, Simon, Knight, David W. and Tan, Wen-Fei (2007) Expedient syntheses of β-iodofurans by 5-endo-dig cyclisations. European Journal of Organic Chemistry, 2007 (34). pp. 5759-5770. ISSN 1434-193X

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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.

Item Type: Article
Faculty \ School: Faculty of Science > School of Chemistry
UEA Research Groups: Faculty of Science > Research Groups > Synthetic Chemistry (former - to 2017)
Faculty of Science > Research Groups > Chemistry of Materials and Catalysis
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Depositing User: Rachel Smith
Date Deposited: 20 Apr 2011 09:08
Last Modified: 24 Oct 2022 01:15
URI: https://ueaeprints.uea.ac.uk/id/eprint/29668
DOI: 10.1002/ejoc.200700681

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