Palladium-Catalysed Isomerisation of 2-Vinylidenehydrofurans to 1,3-Dienes and Some Aspects of Their Reactivity
The transformation of easily accessible 2‐vinylidenehydrofurans into stable 1,3‐dienes has been achieved by using catalytic amounts of palladium(0). These valuable compounds were then engaged in subsequent Diels–Alder reactions giving access to complex heterocyclic cores found in numerous natural pr...
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| Veröffentlicht in: | European Journal of Organic Chemistry 2008-09, Vol.2008 (26), p.4446-4453 |
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| container_issue | 26 |
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| container_title | European Journal of Organic Chemistry |
| container_volume | 2008 |
| creator | Ghobsi, Abdelkader Hacini, Salih Wavrin, Laurence Gaudel-Siri, Anouk Corbères, Agnès Nicolas, Cyril Bonne, Damien Viala, Jacques Rodriguez, Jean |
| description | The transformation of easily accessible 2‐vinylidenehydrofurans into stable 1,3‐dienes has been achieved by using catalytic amounts of palladium(0). These valuable compounds were then engaged in subsequent Diels–Alder reactions giving access to complex heterocyclic cores found in numerous natural products. A rationale for the regioselectivity of the Diels–Alder reactions with vinylfurans has been provided by DFT calculations. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
Palladium has been employed as an efficient catalyst in the isomerisation of easily synthesised vinylidenehydrofurans to the corresponding 1,3‐dienes. When treated with dienophiles, these stable compounds afforded the expected Diels–Alder adducts in good yields and high diastereoselectivities. |
| doi_str_mv | 10.1002/ejoc.200800517 |
| format | Article |
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Palladium has been employed as an efficient catalyst in the isomerisation of easily synthesised vinylidenehydrofurans to the corresponding 1,3‐dienes. When treated with dienophiles, these stable compounds afforded the expected Diels–Alder adducts in good yields and high diastereoselectivities.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.200800517</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Allenes ; Diels-Alder reactions ; Isomerization ; Palladium</subject><ispartof>European Journal of Organic Chemistry, 2008-09, Vol.2008 (26), p.4446-4453</ispartof><rights>Copyright © 2008 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3277-75336c78417364f1831f9b5b32556bc0943712fdee0e8c7abdb3f50cf9d4ae483</citedby><cites>FETCH-LOGICAL-c3277-75336c78417364f1831f9b5b32556bc0943712fdee0e8c7abdb3f50cf9d4ae483</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fejoc.200800517$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.200800517$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>313,314,780,784,792,1416,27913,27915,27916,45565,45566</link.rule.ids></links><search><creatorcontrib>Ghobsi, Abdelkader</creatorcontrib><creatorcontrib>Hacini, Salih</creatorcontrib><creatorcontrib>Wavrin, Laurence</creatorcontrib><creatorcontrib>Gaudel-Siri, Anouk</creatorcontrib><creatorcontrib>Corbères, Agnès</creatorcontrib><creatorcontrib>Nicolas, Cyril</creatorcontrib><creatorcontrib>Bonne, Damien</creatorcontrib><creatorcontrib>Viala, Jacques</creatorcontrib><creatorcontrib>Rodriguez, Jean</creatorcontrib><title>Palladium-Catalysed Isomerisation of 2-Vinylidenehydrofurans to 1,3-Dienes and Some Aspects of Their Reactivity</title><title>European Journal of Organic Chemistry</title><addtitle>Eur. J. Org. Chem</addtitle><description>The transformation of easily accessible 2‐vinylidenehydrofurans into stable 1,3‐dienes has been achieved by using catalytic amounts of palladium(0). These valuable compounds were then engaged in subsequent Diels–Alder reactions giving access to complex heterocyclic cores found in numerous natural products. A rationale for the regioselectivity of the Diels–Alder reactions with vinylfurans has been provided by DFT calculations. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
Palladium has been employed as an efficient catalyst in the isomerisation of easily synthesised vinylidenehydrofurans to the corresponding 1,3‐dienes. When treated with dienophiles, these stable compounds afforded the expected Diels–Alder adducts in good yields and high diastereoselectivities.</description><subject>Allenes</subject><subject>Diels-Alder reactions</subject><subject>Isomerization</subject><subject>Palladium</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><recordid>eNqF0M9PwjAUB_DFaCKiV8_9Ayy-rtu6HslEfoSAUVTipem6NhTHZtqh7r8XgiHePL2Xl-_nHb5BcE2gRwDCW72uVS8ESAFiwk6CDgHOMSQcTnd7RCNMOF2eBxferwGAJwnpBPWDLEtZ2O0GZ7KRZet1gca-3mhnvWxsXaHaoBC_2KotbaErvWoLV5utk5VHTY3IDcV3dnf3SFYFetpJ1PcfWjV-LxcrbR161FI19tM27WVwZmTp9dXv7AbP94NFNsLT-XCc9adY0ZAxzGJKE8XSiDCaRIaklBiexzkN4zjJFfCIMhKaQmvQqWIyL3JqYlCGF5HUUUq7Qe_wV7nae6eN-HB2I10rCIh9XWJflzjWtQP8AL5sqdt_0mIwmWd_LT5Y6xv9fbTSvYuEURaL19lQpKNJ9kbYUszoD3USfxU</recordid><startdate>200809</startdate><enddate>200809</enddate><creator>Ghobsi, Abdelkader</creator><creator>Hacini, Salih</creator><creator>Wavrin, Laurence</creator><creator>Gaudel-Siri, Anouk</creator><creator>Corbères, Agnès</creator><creator>Nicolas, Cyril</creator><creator>Bonne, Damien</creator><creator>Viala, Jacques</creator><creator>Rodriguez, Jean</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>200809</creationdate><title>Palladium-Catalysed Isomerisation of 2-Vinylidenehydrofurans to 1,3-Dienes and Some Aspects of Their Reactivity</title><author>Ghobsi, Abdelkader ; Hacini, Salih ; Wavrin, Laurence ; Gaudel-Siri, Anouk ; Corbères, Agnès ; Nicolas, Cyril ; Bonne, Damien ; Viala, Jacques ; Rodriguez, Jean</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3277-75336c78417364f1831f9b5b32556bc0943712fdee0e8c7abdb3f50cf9d4ae483</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>Allenes</topic><topic>Diels-Alder reactions</topic><topic>Isomerization</topic><topic>Palladium</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ghobsi, Abdelkader</creatorcontrib><creatorcontrib>Hacini, Salih</creatorcontrib><creatorcontrib>Wavrin, Laurence</creatorcontrib><creatorcontrib>Gaudel-Siri, Anouk</creatorcontrib><creatorcontrib>Corbères, Agnès</creatorcontrib><creatorcontrib>Nicolas, Cyril</creatorcontrib><creatorcontrib>Bonne, Damien</creatorcontrib><creatorcontrib>Viala, Jacques</creatorcontrib><creatorcontrib>Rodriguez, Jean</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><jtitle>European Journal of Organic Chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ghobsi, Abdelkader</au><au>Hacini, Salih</au><au>Wavrin, Laurence</au><au>Gaudel-Siri, Anouk</au><au>Corbères, Agnès</au><au>Nicolas, Cyril</au><au>Bonne, Damien</au><au>Viala, Jacques</au><au>Rodriguez, Jean</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Palladium-Catalysed Isomerisation of 2-Vinylidenehydrofurans to 1,3-Dienes and Some Aspects of Their Reactivity</atitle><jtitle>European Journal of Organic Chemistry</jtitle><addtitle>Eur. J. Org. Chem</addtitle><date>2008-09</date><risdate>2008</risdate><volume>2008</volume><issue>26</issue><spage>4446</spage><epage>4453</epage><pages>4446-4453</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>The transformation of easily accessible 2‐vinylidenehydrofurans into stable 1,3‐dienes has been achieved by using catalytic amounts of palladium(0). These valuable compounds were then engaged in subsequent Diels–Alder reactions giving access to complex heterocyclic cores found in numerous natural products. A rationale for the regioselectivity of the Diels–Alder reactions with vinylfurans has been provided by DFT calculations. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
Palladium has been employed as an efficient catalyst in the isomerisation of easily synthesised vinylidenehydrofurans to the corresponding 1,3‐dienes. When treated with dienophiles, these stable compounds afforded the expected Diels–Alder adducts in good yields and high diastereoselectivities.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/ejoc.200800517</doi><tpages>8</tpages></addata></record> |
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| identifier | ISSN: 1434-193X |
| ispartof | European Journal of Organic Chemistry, 2008-09, Vol.2008 (26), p.4446-4453 |
| issn | 1434-193X 1099-0690 |
| language | eng |
| recordid | cdi_crossref_primary_10_1002_ejoc_200800517 |
| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Allenes Diels-Alder reactions Isomerization Palladium |
| title | Palladium-Catalysed Isomerisation of 2-Vinylidenehydrofurans to 1,3-Dienes and Some Aspects of Their Reactivity |
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