Dicobaltoctacarbonyl-Mediated Synthesis of Tricyclic 5,6-Diydropyran-2-one Derivatives via Tandem Cycloaddition Reaction between cis-Epoxyalkynes, a Tethered Olefin, and Carbon Monoxide
Identifieur interne : 000E94 ( Main/Exploration ); précédent : 000E93; suivant : 000E95Dicobaltoctacarbonyl-Mediated Synthesis of Tricyclic 5,6-Diydropyran-2-one Derivatives via Tandem Cycloaddition Reaction between cis-Epoxyalkynes, a Tethered Olefin, and Carbon Monoxide
Auteurs : Arjan Odedra [République populaire de Chine] ; Shie-Fu Lush [République populaire de Chine] ; Rai-Shung Liu [République populaire de Chine]Source :
- The Journal of Organic Chemistry [ 0022-3263 ] ; 2006.
Abstract
Cobalt carbonyl complex Co2(CO)8 implemented an intramolecular carbonylation of cis-epoxyalkynes to generate Co2(CO)6-stabilized γ-lactonyl allene species. For 1,1,2-trisubstituted epoxyalkynes, this Co2(CO)6-allene species reacted with a tethered olefin to give [2 + 2]-cycloadducts, and with CO and a tethered olefin to produce [2 + 2 + 1]-cycloadducts. These resulting cycloadducts have a 5,6-diydropyran-2-one core fused with a cyclobutane and a cyclopentanone ring, respectively. For 1,2-disubstituted cis-epoxyalkyne and 1,1,2-trisubstituted cis-epoxyalkynes bearing a heteroatom constituent, cyclization of the corresponding epoxyalkyne with a tethered alkene is invariably accompanied by incorporation of CO to produce a [2 + 2 + 1]-cycloadduct, even in the absence of CO. We have prepared various 1,1,2-trisubstituted and 1,2-disubstituted cis-epoxyalkynes to generalize such cycloaddition pathways. Attempt to use an organic promoter to perform these tandem cycloadditions was unsuccessful because of a competing Pauson−Khand reaction. Cyclization of a 1,2-disubstituted epoxyalkyne with a tethered diene was achieved successfully in one case, but the yield was low (25%).
Url:
DOI: 10.1021/jo0620617
Affiliations:
Links toward previous steps (curation, corpus...)
- to stream Istex, to step Corpus: 000523
- to stream Istex, to step Curation: 000503
- to stream Istex, to step Checkpoint: 000179
- to stream Main, to step Merge: 000F00
- to stream Main, to step Curation: 000E94
Le document en format XML
<record><TEI wicri:istexFullTextTei="biblStruct"><teiHeader><fileDesc><titleStmt><title>Dicobaltoctacarbonyl-Mediated Synthesis of Tricyclic 5,6-Diydropyran-2-one Derivatives via Tandem Cycloaddition Reaction between cis-Epoxyalkynes, a Tethered Olefin, and Carbon Monoxide</title><author><name sortKey="Odedra, Arjan" sort="Odedra, Arjan" uniqKey="Odedra A" first="Arjan" last="Odedra">Arjan Odedra</name></author><author><name sortKey="Lush, Shie Fu" sort="Lush, Shie Fu" uniqKey="Lush S" first="Shie-Fu" last="Lush">Shie-Fu Lush</name></author><author><name sortKey="Liu, Rai Shung" sort="Liu, Rai Shung" uniqKey="Liu R" first="Rai-Shung" last="Liu">Rai-Shung Liu</name></author></titleStmt><publicationStmt><idno type="wicri:source">ISTEX</idno><idno type="RBID">ISTEX:EABE33257BFF47EA6412F52F4BAABC6F040F4902</idno><date when="2007" year="2007">2007</date><idno type="doi">10.1021/jo0620617</idno><idno type="url">https://api.istex.fr/ark:/67375/TPS-WH0VP5X4-3/fulltext.pdf</idno><idno type="wicri:Area/Istex/Corpus">000523</idno><idno type="wicri:explorRef" wicri:stream="Istex" wicri:step="Corpus" wicri:corpus="ISTEX">000523</idno><idno type="wicri:Area/Istex/Curation">000503</idno><idno type="wicri:Area/Istex/Checkpoint">000179</idno><idno type="wicri:explorRef" wicri:stream="Istex" wicri:step="Checkpoint">000179</idno><idno type="wicri:doubleKey">0022-3263:2007:Odedra A:dicobaltoctacarbonyl:mediated:synthesis</idno><idno type="wicri:Area/Main/Merge">000F00</idno><idno type="wicri:Area/Main/Curation">000E94</idno><idno type="wicri:Area/Main/Exploration">000E94</idno></publicationStmt><sourceDesc><biblStruct><analytic><title level="a" type="main" xml:lang="en">Dicobaltoctacarbonyl-Mediated Synthesis of Tricyclic
5,6-Diydropyran-2-one Derivatives via Tandem Cycloaddition
Reaction between <hi rend="italic">cis</hi>-Epoxyalkynes, a Tethered Olefin, and
Carbon Monoxide</title><author><name sortKey="Odedra, Arjan" sort="Odedra, Arjan" uniqKey="Odedra A" first="Arjan" last="Odedra">Arjan Odedra</name><affiliation wicri:level="1"><country xml:lang="fr" wicri:curation="lc">République populaire de Chine</country><wicri:regionArea>Department of Chemistry, National Tsing-Hua University, Hsinchu, Taiwan, ROC and Department ofMedicinal Technology, Yuanpei University, Hsinchu, Taiwan 30043</wicri:regionArea><wicri:noRegion>Taiwan 30043</wicri:noRegion></affiliation><affiliation></affiliation></author><author><name sortKey="Lush, Shie Fu" sort="Lush, Shie Fu" uniqKey="Lush S" first="Shie-Fu" last="Lush">Shie-Fu Lush</name><affiliation wicri:level="1"><country xml:lang="fr" wicri:curation="lc">République populaire de Chine</country><wicri:regionArea>Department of Chemistry, National Tsing-Hua University, Hsinchu, Taiwan, ROC and Department ofMedicinal Technology, Yuanpei University, Hsinchu, Taiwan 30043</wicri:regionArea><wicri:noRegion>Taiwan 30043</wicri:noRegion></affiliation><affiliation></affiliation></author><author><name sortKey="Liu, Rai Shung" sort="Liu, Rai Shung" uniqKey="Liu R" first="Rai-Shung" last="Liu">Rai-Shung Liu</name><affiliation wicri:level="1"><country xml:lang="fr" wicri:curation="lc">République populaire de Chine</country><wicri:regionArea>Department of Chemistry, National Tsing-Hua University, Hsinchu, Taiwan, ROC and Department ofMedicinal Technology, Yuanpei University, Hsinchu, Taiwan 30043</wicri:regionArea><wicri:noRegion>Taiwan 30043</wicri:noRegion></affiliation><affiliation></affiliation><affiliation></affiliation></author></analytic><monogr></monogr><series><title level="j" type="main">The Journal of Organic Chemistry</title><title level="j" type="abbrev">J. Org. Chem.</title><idno type="ISSN">0022-3263</idno><idno type="eISSN">1520-6904</idno><imprint><publisher>American Chemical Society</publisher><date type="e-published" when="2006-12-13">2006</date><date when="2007-01-19">2007</date><biblScope unit="vol">72</biblScope><biblScope unit="issue">2</biblScope><biblScope unit="page" from="567">567</biblScope><biblScope unit="page" to="573">573</biblScope></imprint><idno type="ISSN">0022-3263</idno></series></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">0022-3263</idno></seriesStmt></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract">Cobalt carbonyl complex Co2(CO)8 implemented an intramolecular carbonylation of cis-epoxyalkynes to generate Co2(CO)6-stabilized γ-lactonyl allene species. For 1,1,2-trisubstituted epoxyalkynes, this Co2(CO)6-allene species reacted with a tethered olefin to give [2 + 2]-cycloadducts, and with CO and a tethered olefin to produce [2 + 2 + 1]-cycloadducts. These resulting cycloadducts have a 5,6-diydropyran-2-one core fused with a cyclobutane and a cyclopentanone ring, respectively. For 1,2-disubstituted cis-epoxyalkyne and 1,1,2-trisubstituted cis-epoxyalkynes bearing a heteroatom constituent, cyclization of the corresponding epoxyalkyne with a tethered alkene is invariably accompanied by incorporation of CO to produce a [2 + 2 + 1]-cycloadduct, even in the absence of CO. We have prepared various 1,1,2-trisubstituted and 1,2-disubstituted cis-epoxyalkynes to generalize such cycloaddition pathways. Attempt to use an organic promoter to perform these tandem cycloadditions was unsuccessful because of a competing Pauson−Khand reaction. Cyclization of a 1,2-disubstituted epoxyalkyne with a tethered diene was achieved successfully in one case, but the yield was low (25%).</div></front></TEI><affiliations><list><country><li>République populaire de Chine</li></country></list><tree><country name="République populaire de Chine"><noRegion><name sortKey="Odedra, Arjan" sort="Odedra, Arjan" uniqKey="Odedra A" first="Arjan" last="Odedra">Arjan Odedra</name></noRegion><name sortKey="Liu, Rai Shung" sort="Liu, Rai Shung" uniqKey="Liu R" first="Rai-Shung" last="Liu">Rai-Shung Liu</name><name sortKey="Lush, Shie Fu" sort="Lush, Shie Fu" uniqKey="Lush S" first="Shie-Fu" last="Lush">Shie-Fu Lush</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
EXPLOR_STEP=$WICRI_ROOT/Wicri/Sante/explor/CovidV1/Data/Main/Exploration
HfdSelect -h $EXPLOR_STEP/biblio.hfd -nk 000E94 | SxmlIndent | more
Ou
HfdSelect -h $EXPLOR_AREA/Data/Main/Exploration/biblio.hfd -nk 000E94 | SxmlIndent | more
Pour mettre un lien sur cette page dans le réseau Wicri
{{Explor lien
|wiki= Wicri/Sante
|area= CovidV1
|flux= Main
|étape= Exploration
|type= RBID
|clé= ISTEX:EABE33257BFF47EA6412F52F4BAABC6F040F4902
|texte= Dicobaltoctacarbonyl-Mediated Synthesis of Tricyclic 5,6-Diydropyran-2-one Derivatives via Tandem Cycloaddition Reaction between cis-Epoxyalkynes, a Tethered Olefin, and Carbon Monoxide
}}
| This area was generated with Dilib version V0.6.33. |  |