Expedient Syntheses of β-Iodofurans by 5-endo-dig Cyclisations
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 a...
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| Published in | European Journal of Organic Chemistry Vol. 2007; no. 34; pp. 5759 - 5770 |
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| Main Authors | , , , , |
| Format | Book Review Journal Article |
| Language | English |
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Weinheim
WILEY-VCH Verlag
01.12.2007
WILEY‐VCH Verlag Wiley |
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| 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, 69451 Weinheim, Germany, 2007) |
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| AbstractList | 5-endo-dig cyclisations of 3-alkyne-1,2-diols using iodine as the electrophile proceed smoothly to deliver excellent yields of the corresponding beta-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 a-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. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007). 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, 69451 Weinheim, Germany, 2007) 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, 69451 Weinheim, Germany, 2007) |
| Author | El-Taeb, Gamila M. M. Jones, Simon Bew, Sean P. Tan, Wen-Fei Knight, David W. |
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| ContentType | Book Review Journal Article |
| Copyright | Copyright © 2007 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim |
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| Keywords | ELECTROPHILIC CYCLIZATION 2-(1-ALKYNYL)-2-ALKEN-1-ONES ACETYLENE furans cyclisation ALKYNES DERIVATIVES SALTS INTRAMOLECULAR ADDITION iodocyclisation |
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| PublicationTitle | European Journal of Organic Chemistry |
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| Snippet | 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.... 5-endo-dig cyclisations of 3-alkyne-1,2-diols using iodine as the electrophile proceed smoothly to deliver excellent yields of the corresponding... 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... |
| Source | Web of Science |
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| StartPage | 5759 |
| SubjectTerms | Chemistry Chemistry, Organic Cyclisation Furans Iodocyclisation Physical Sciences Science & Technology |
| Title | Expedient Syntheses of β-Iodofurans by 5-endo-dig Cyclisations |
| URI | https://api.istex.fr/ark:/67375/WNG-BWW00SG3-7/fulltext.pdf https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fejoc.200700681 http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000251384000014 |
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