A formal [3 + 3] cycloaddition reaction. Improved reactivity using alpha,beta-unsaturated iminium salts and evidence for reversibility of 6pi-electron electrocyclic ring closure of 1-oxatrienes
A detailed account regarding a formal [3 + 3] cycloaddition method using 4-hydroxy-2-pyrones and 1,3-diketones is described here. This formal cycloaddition reaction or annulation reaction is synthetically useful for constructing 2H-pyranyl heterocycles. The usage of alpha,beta-unsaturated iminium sa...
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| Veröffentlicht in: | Journal of organic chemistry 2003-03, Vol.68 (5), p.1729-1735 |
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| container_title | Journal of organic chemistry |
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| creator | Shen, Hong C Wang, Jiashi Cole, Kevin P McLaughlin, Michael J Morgan, Christopher D Douglas, Christopher J Hsung, Richard P Coverdale, Heather A Gerasyuto, Aleksey I Hahn, Juliet M Liu, Jia Sklenicka, Heather M Wei, Lin-Li Zehnder, Luke R Zificsak, Craig A |
| description | A detailed account regarding a formal [3 + 3] cycloaddition method using 4-hydroxy-2-pyrones and 1,3-diketones is described here. This formal cycloaddition reaction or annulation reaction is synthetically useful for constructing 2H-pyranyl heterocycles. The usage of alpha,beta-unsaturated iminium salts is significant in controlling competing reaction pathways to give exclusively 2H-pyrans. Most significantly, experimental evidence is provided to support the mechanism of this reaction that involves a sequential Knoevenagel condensation and a reversible 6pi-electron electrocyclic ring-closure of 1-oxatrienes. |
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Improved reactivity using alpha,beta-unsaturated iminium salts and evidence for reversibility of 6pi-electron electrocyclic ring closure of 1-oxatrienes</title><source>ACS Publications</source><source>MEDLINE</source><creator>Shen, Hong C ; Wang, Jiashi ; Cole, Kevin P ; McLaughlin, Michael J ; Morgan, Christopher D ; Douglas, Christopher J ; Hsung, Richard P ; Coverdale, Heather A ; Gerasyuto, Aleksey I ; Hahn, Juliet M ; Liu, Jia ; Sklenicka, Heather M ; Wei, Lin-Li ; Zehnder, Luke R ; Zificsak, Craig A</creator><creatorcontrib>Shen, Hong C ; Wang, Jiashi ; Cole, Kevin P ; McLaughlin, Michael J ; Morgan, Christopher D ; Douglas, Christopher J ; Hsung, Richard P ; Coverdale, Heather A ; Gerasyuto, Aleksey I ; Hahn, Juliet M ; Liu, Jia ; Sklenicka, Heather M ; Wei, Lin-Li ; Zehnder, Luke R ; Zificsak, Craig A</creatorcontrib><description>A detailed account regarding a formal [3 + 3] cycloaddition method using 4-hydroxy-2-pyrones and 1,3-diketones is described here. 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Most significantly, experimental evidence is provided to support the mechanism of this reaction that involves a sequential Knoevenagel condensation and a reversible 6pi-electron electrocyclic ring-closure of 1-oxatrienes.</description><subject>Alkenes - chemistry</subject><subject>Catalysis</subject><subject>Chemistry, Organic - methods</subject><subject>Crystallography, X-Ray</subject><subject>Cyclization</subject><subject>Imines - chemistry</subject><subject>Indicators and Reagents</subject><subject>Ketones - chemistry</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Molecular Structure</subject><subject>Oxidation-Reduction</subject><subject>Pyrans - chemical synthesis</subject><subject>Pyrones - chemistry</subject><subject>Salts - chemical synthesis</subject><subject>Stereoisomerism</subject><issn>0022-3263</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2003</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNo1UMtKxEAQzEFx19VfkDl50cgkk5lkj8viY0HwsjeR0Jl0dGQyifMI7uf5Z05wbRq6aIqqok6SJaV5nrJcsEVy7twnjcM5P0sWWS5oVVZ8mfxsSDfYHjR5ZeSGsDciD1IP0LbKq8EQiyBncEd2_WiHCdvja1L-QIJT5p2AHj_gtkEPaTAOfLDgI0_1yqjQEwfaOwKmJTipFo3E2TLKTGidapSelYaOiFGlqFF6G32PYA6jJLGzTYzlgsWZmqXDN3ir0KC7SE470A4vj3eV7B_u99un9PnlcbfdPKcjL3gqKe2yPMt5B5lAWja0WZcopZBd0UAuMyoLsW4aCQKhYpJzhlwUHcvKjq-riq2S6z_Z2MJXQOfrXjmJWoPBIbi6ZFTEpZF4dSSGpse2Hq3qwR7q_87ZL8EDgVQ</recordid><startdate>20030307</startdate><enddate>20030307</enddate><creator>Shen, Hong C</creator><creator>Wang, Jiashi</creator><creator>Cole, Kevin P</creator><creator>McLaughlin, Michael J</creator><creator>Morgan, Christopher D</creator><creator>Douglas, Christopher J</creator><creator>Hsung, Richard P</creator><creator>Coverdale, Heather A</creator><creator>Gerasyuto, Aleksey I</creator><creator>Hahn, Juliet M</creator><creator>Liu, Jia</creator><creator>Sklenicka, Heather M</creator><creator>Wei, Lin-Li</creator><creator>Zehnder, Luke R</creator><creator>Zificsak, Craig A</creator><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>7X8</scope></search><sort><creationdate>20030307</creationdate><title>A formal [3 + 3] cycloaddition reaction. 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Improved reactivity using alpha,beta-unsaturated iminium salts and evidence for reversibility of 6pi-electron electrocyclic ring closure of 1-oxatrienes</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J Org Chem</addtitle><date>2003-03-07</date><risdate>2003</risdate><volume>68</volume><issue>5</issue><spage>1729</spage><epage>1735</epage><pages>1729-1735</pages><issn>0022-3263</issn><abstract>A detailed account regarding a formal [3 + 3] cycloaddition method using 4-hydroxy-2-pyrones and 1,3-diketones is described here. This formal cycloaddition reaction or annulation reaction is synthetically useful for constructing 2H-pyranyl heterocycles. The usage of alpha,beta-unsaturated iminium salts is significant in controlling competing reaction pathways to give exclusively 2H-pyrans. Most significantly, experimental evidence is provided to support the mechanism of this reaction that involves a sequential Knoevenagel condensation and a reversible 6pi-electron electrocyclic ring-closure of 1-oxatrienes.</abstract><cop>United States</cop><pmid>12608785</pmid><tpages>7</tpages></addata></record> |
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| source | ACS Publications; MEDLINE |
| subjects | Alkenes - chemistry Catalysis Chemistry, Organic - methods Crystallography, X-Ray Cyclization Imines - chemistry Indicators and Reagents Ketones - chemistry Magnetic Resonance Spectroscopy Molecular Structure Oxidation-Reduction Pyrans - chemical synthesis Pyrones - chemistry Salts - chemical synthesis Stereoisomerism |
| title | A formal [3 + 3] cycloaddition reaction. Improved reactivity using alpha,beta-unsaturated iminium salts and evidence for reversibility of 6pi-electron electrocyclic ring closure of 1-oxatrienes |
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