Catalytic Intermolecular Aldehyde−Ketone Coupling via Acyl Phosphonates
The first catalytic intermolecular aldehyde−ketone coupling via acyl phosphonate is reported. Acyl phosphonates are potent acyl anion precursors, which generate acyl anion equivalents under the influence of cyanide anion via phosphonate−phosphate rearrangement. These anions readily react with activa...
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| Veröffentlicht in: | Journal of organic chemistry 2009-03, Vol.74 (5), p.2197-2199 |
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| container_end_page | 2199 |
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| container_issue | 5 |
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| container_title | Journal of organic chemistry |
| container_volume | 74 |
| creator | Demir, Ayhan S Esiringü, lker Göllü, Mehmet Reis, Ömer |
| description | The first catalytic intermolecular aldehyde−ketone coupling via acyl phosphonate is reported. Acyl phosphonates are potent acyl anion precursors, which generate acyl anion equivalents under the influence of cyanide anion via phosphonate−phosphate rearrangement. These anions readily react with activated ketones to form acyloin type coupling in 41−95% yields. |
| doi_str_mv | 10.1021/jo8026627 |
| format | Article |
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Acyl phosphonates are potent acyl anion precursors, which generate acyl anion equivalents under the influence of cyanide anion via phosphonate−phosphate rearrangement. 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Org. Chem</addtitle><description>The first catalytic intermolecular aldehyde−ketone coupling via acyl phosphonate is reported. Acyl phosphonates are potent acyl anion precursors, which generate acyl anion equivalents under the influence of cyanide anion via phosphonate−phosphate rearrangement. These anions readily react with activated ketones to form acyloin type coupling in 41−95% yields.</description><subject>Aldehydes - chemistry</subject><subject>Aliphatic compounds</subject><subject>Catalysis</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Ketones - chemistry</subject><subject>Molecular Structure</subject><subject>Organic chemistry</subject><subject>Organophosphonates - chemistry</subject><subject>Preparations and properties</subject><subject>Stereoisomerism</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0LtOwzAUBmALgWgpDLwAyoIQQ8CX-DZWEZeKSjDAHDmOQ1M5cbETpLwBM4_IkxDUqF04y1m-8x_pB-AcwRsEMbpdOwExY5gfgCmiGMZMwuQQTCHEOCaYkQk4CWENh6GUHoMJkkjK4WAKFqlqle3bSkeLpjW-dtboziofzW1hVn1hfr6-n0zrGhOlrtvYqnmPPisVzXVvo5eVC5uVa1Rrwik4KpUN5mzcM_B2f_eaPsbL54dFOl_GKkGwjYnMOU0IKWWuklLngmNGRcIKCbkphZQFR0lhMJJ5nlOuiMSClIVhPNEsh5TMwNU2d-PdR2dCm9VV0MZa1RjXhYwTgogQggzyeiu1dyF4U2YbX9XK9xmC2V9x2a64wV6MqV1em2Ivx6YGcDkCFbSypVeNrsLOYYQhk0zsndJhyO98M5Txz8Nf5haBXw</recordid><startdate>20090306</startdate><enddate>20090306</enddate><creator>Demir, Ayhan S</creator><creator>Esiringü, lker</creator><creator>Göllü, Mehmet</creator><creator>Reis, Ömer</creator><general>American Chemical Society</general><scope>IQODW</scope><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>20090306</creationdate><title>Catalytic Intermolecular Aldehyde−Ketone Coupling via Acyl Phosphonates</title><author>Demir, Ayhan S ; Esiringü, lker ; Göllü, Mehmet ; Reis, Ömer</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a410t-39b75433f9ba4fcb87265846d907ef899d714de219bbb57a39283fde674c6b053</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>Aldehydes - chemistry</topic><topic>Aliphatic compounds</topic><topic>Catalysis</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Ketones - chemistry</topic><topic>Molecular Structure</topic><topic>Organic chemistry</topic><topic>Organophosphonates - chemistry</topic><topic>Preparations and properties</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Demir, Ayhan S</creatorcontrib><creatorcontrib>Esiringü, lker</creatorcontrib><creatorcontrib>Göllü, Mehmet</creatorcontrib><creatorcontrib>Reis, Ömer</creatorcontrib><collection>Pascal-Francis</collection><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>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Demir, Ayhan S</au><au>Esiringü, lker</au><au>Göllü, Mehmet</au><au>Reis, Ömer</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Catalytic Intermolecular Aldehyde−Ketone Coupling via Acyl Phosphonates</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2009-03-06</date><risdate>2009</risdate><volume>74</volume><issue>5</issue><spage>2197</spage><epage>2199</epage><pages>2197-2199</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>The first catalytic intermolecular aldehyde−ketone coupling via acyl phosphonate is reported. Acyl phosphonates are potent acyl anion precursors, which generate acyl anion equivalents under the influence of cyanide anion via phosphonate−phosphate rearrangement. These anions readily react with activated ketones to form acyloin type coupling in 41−95% yields.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>19199662</pmid><doi>10.1021/jo8026627</doi><tpages>3</tpages></addata></record> |
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| ispartof | Journal of organic chemistry, 2009-03, Vol.74 (5), p.2197-2199 |
| issn | 0022-3263 1520-6904 |
| language | eng |
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| source | MEDLINE; ACS Publications |
| subjects | Aldehydes - chemistry Aliphatic compounds Catalysis Chemistry Exact sciences and technology Ketones - chemistry Molecular Structure Organic chemistry Organophosphonates - chemistry Preparations and properties Stereoisomerism |
| title | Catalytic Intermolecular Aldehyde−Ketone Coupling via Acyl Phosphonates |
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