Palladacycle-Catalyzed Reaction of Bicyclic Alkenes with Terminal Ynones: Regiospecific Synthesis of Polysubstituted Furans
A new synthetic strategy to access polysubstituted furans regiospecifically has been developed using simple bicyclic alkenes and terminal ynones as starting materials with palladacycles as unique active catalysts. A rational mechanism has also been proposed. This reaction features mild reaction cond...
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| Veröffentlicht in: | Organic letters 2012-11, Vol.14 (22), p.5756-5759 |
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| container_end_page | 5759 |
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| container_issue | 22 |
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| container_title | Organic letters |
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| creator | Ge, Guang-Cun Mo, Dong-Liang Ding, Chang-Hua Dai, Li-Xin Hou, Xue-Long |
| description | A new synthetic strategy to access polysubstituted furans regiospecifically has been developed using simple bicyclic alkenes and terminal ynones as starting materials with palladacycles as unique active catalysts. A rational mechanism has also been proposed. This reaction features mild reaction conditions, easily available starting materials and palladacycle catalysts, a wide substrate scope, and high regiospecificity. |
| doi_str_mv | 10.1021/ol302586m |
| format | Article |
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A rational mechanism has also been proposed. This reaction features mild reaction conditions, easily available starting materials and palladacycle catalysts, a wide substrate scope, and high regiospecificity.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/ol302586m</identifier><identifier>PMID: 23145937</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Alkenes - chemistry ; Catalysis ; Furans - chemical synthesis ; Furans - chemistry ; Ketones - chemical synthesis ; Ketones - chemistry ; Molecular Structure ; Palladium ; Stereoisomerism</subject><ispartof>Organic letters, 2012-11, Vol.14 (22), p.5756-5759</ispartof><rights>Copyright © 2012 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a315t-6b94f863c1727e13170090449bb284ec2eb4118269ae687efbe125cbbb196eaa3</citedby><cites>FETCH-LOGICAL-a315t-6b94f863c1727e13170090449bb284ec2eb4118269ae687efbe125cbbb196eaa3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/ol302586m$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ol302586m$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/23145937$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ge, Guang-Cun</creatorcontrib><creatorcontrib>Mo, Dong-Liang</creatorcontrib><creatorcontrib>Ding, Chang-Hua</creatorcontrib><creatorcontrib>Dai, Li-Xin</creatorcontrib><creatorcontrib>Hou, Xue-Long</creatorcontrib><title>Palladacycle-Catalyzed Reaction of Bicyclic Alkenes with Terminal Ynones: Regiospecific Synthesis of Polysubstituted Furans</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>A new synthetic strategy to access polysubstituted furans regiospecifically has been developed using simple bicyclic alkenes and terminal ynones as starting materials with palladacycles as unique active catalysts. A rational mechanism has also been proposed. This reaction features mild reaction conditions, easily available starting materials and palladacycle catalysts, a wide substrate scope, and high regiospecificity.</description><subject>Alkenes - chemistry</subject><subject>Catalysis</subject><subject>Furans - chemical synthesis</subject><subject>Furans - chemistry</subject><subject>Ketones - chemical synthesis</subject><subject>Ketones - chemistry</subject><subject>Molecular Structure</subject><subject>Palladium</subject><subject>Stereoisomerism</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkE1PGzEQhq2KqoG0h_4BtBekcljq8X73FqIGkJCI2vTQ08p2ZsHUuw47XqEtfx5HCTlxmtHMM480L2NfgV8AF_Dd2YSLrMzbD-wYMpHEBc_E0aHP-YSdED1yDmFSfWITkUCaVUlxzF6W0lq5lnrUFuO59NKO_3Ed_UKpvXFd5Jro0my3Rkcz-w87pOjZ-IdohX1rOmmjv50Lwx_h5N442qA2TWB_j51_QDK0NSydHWlQ5I0ffLAvhl529Jl9bKQl_LKvU_Zn8XM1v45v765u5rPbWCaQ-ThXVdqUeaKhEAVCAgXnFU_TSilRpqgFqhSgFHklMS8LbBSCyLRSCqocpUym7NvOu-nd04Dk69aQxvB3h26gGqCAMgdeZgE936G6d0Q9NvWmN63sxxp4vc26PmQd2NO9dlAtrg_kW7gBONsBUlP96IY-pEXviF4BF1OHVg</recordid><startdate>20121116</startdate><enddate>20121116</enddate><creator>Ge, Guang-Cun</creator><creator>Mo, Dong-Liang</creator><creator>Ding, Chang-Hua</creator><creator>Dai, Li-Xin</creator><creator>Hou, Xue-Long</creator><general>American Chemical Society</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20121116</creationdate><title>Palladacycle-Catalyzed Reaction of Bicyclic Alkenes with Terminal Ynones: Regiospecific Synthesis of Polysubstituted Furans</title><author>Ge, Guang-Cun ; Mo, Dong-Liang ; Ding, Chang-Hua ; Dai, Li-Xin ; Hou, Xue-Long</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a315t-6b94f863c1727e13170090449bb284ec2eb4118269ae687efbe125cbbb196eaa3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Alkenes - chemistry</topic><topic>Catalysis</topic><topic>Furans - chemical synthesis</topic><topic>Furans - chemistry</topic><topic>Ketones - chemical synthesis</topic><topic>Ketones - chemistry</topic><topic>Molecular Structure</topic><topic>Palladium</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ge, Guang-Cun</creatorcontrib><creatorcontrib>Mo, Dong-Liang</creatorcontrib><creatorcontrib>Ding, Chang-Hua</creatorcontrib><creatorcontrib>Dai, Li-Xin</creatorcontrib><creatorcontrib>Hou, Xue-Long</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ge, Guang-Cun</au><au>Mo, Dong-Liang</au><au>Ding, Chang-Hua</au><au>Dai, Li-Xin</au><au>Hou, Xue-Long</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Palladacycle-Catalyzed Reaction of Bicyclic Alkenes with Terminal Ynones: Regiospecific Synthesis of Polysubstituted Furans</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2012-11-16</date><risdate>2012</risdate><volume>14</volume><issue>22</issue><spage>5756</spage><epage>5759</epage><pages>5756-5759</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>A new synthetic strategy to access polysubstituted furans regiospecifically has been developed using simple bicyclic alkenes and terminal ynones as starting materials with palladacycles as unique active catalysts. A rational mechanism has also been proposed. This reaction features mild reaction conditions, easily available starting materials and palladacycle catalysts, a wide substrate scope, and high regiospecificity.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>23145937</pmid><doi>10.1021/ol302586m</doi><tpages>4</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1523-7060 |
| ispartof | Organic letters, 2012-11, Vol.14 (22), p.5756-5759 |
| issn | 1523-7060 1523-7052 |
| language | eng |
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| source | ACS Publications; MEDLINE |
| subjects | Alkenes - chemistry Catalysis Furans - chemical synthesis Furans - chemistry Ketones - chemical synthesis Ketones - chemistry Molecular Structure Palladium Stereoisomerism |
| title | Palladacycle-Catalyzed Reaction of Bicyclic Alkenes with Terminal Ynones: Regiospecific Synthesis of Polysubstituted Furans |
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