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Article: Ruthenium(II) porphyrin catalyzed formation of (Z)-4-alkyloxycarbonyl-methylidene-1,3-dioxolanes from γ-alkoxy-γ-diazo-β-ketoesters

TitleRuthenium(II) porphyrin catalyzed formation of (Z)-4-alkyloxycarbonyl-methylidene-1,3-dioxolanes from γ-alkoxy-γ-diazo-β-ketoesters
Authors
Issue Date2002
PublisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/journals/orlef7/index.html
Citation
Organic Letters, 2002, v. 4 n. 6, p. 889-892 How to Cite?
Abstract(equation presented) R 1 = aryl, allyl R 2= methyl, 2,4-dimethyl-3-pentyl and (-)-menthyl Ruthenum(II) porphyrins and dirhodium(II) acetate catalyze cyclization of γ-alkoxy-α-diazo-β-ketoesters to (Z)-4-(alkyloxycarbonylmethylidene)-1,3-dioxolanes selectively (ca. 68% yield) with no formation of 3(2H)-furanones. Reacting a diazo ketoester with [Ru II(TTP)(CO)] [H 2TTP = meso-tetrakis(p-tolyl) porphyrin] in toluene afforded a ruthenium carbenoid complex, which has been isolated and spectroscopically characterized. A mechanism involving hydrogen atom migration from the C-H bond to the ruthenium carbenoid is proposed.
Persistent Identifierhttp://hdl.handle.net/10722/167319
ISSN
2015 Impact Factor: 6.732
2015 SCImago Journal Rankings: 3.187
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorZheng, SLen_US
dc.contributor.authorYu, WYen_US
dc.contributor.authorChe, CMen_US
dc.date.accessioned2012-10-08T03:05:36Z-
dc.date.available2012-10-08T03:05:36Z-
dc.date.issued2002en_US
dc.identifier.citationOrganic Letters, 2002, v. 4 n. 6, p. 889-892en_US
dc.identifier.issn1523-7060en_US
dc.identifier.urihttp://hdl.handle.net/10722/167319-
dc.description.abstract(equation presented) R 1 = aryl, allyl R 2= methyl, 2,4-dimethyl-3-pentyl and (-)-menthyl Ruthenum(II) porphyrins and dirhodium(II) acetate catalyze cyclization of γ-alkoxy-α-diazo-β-ketoesters to (Z)-4-(alkyloxycarbonylmethylidene)-1,3-dioxolanes selectively (ca. 68% yield) with no formation of 3(2H)-furanones. Reacting a diazo ketoester with [Ru II(TTP)(CO)] [H 2TTP = meso-tetrakis(p-tolyl) porphyrin] in toluene afforded a ruthenium carbenoid complex, which has been isolated and spectroscopically characterized. A mechanism involving hydrogen atom migration from the C-H bond to the ruthenium carbenoid is proposed.en_US
dc.languageengen_US
dc.publisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/journals/orlef7/index.htmlen_US
dc.relation.ispartofOrganic Lettersen_US
dc.titleRuthenium(II) porphyrin catalyzed formation of (Z)-4-alkyloxycarbonyl-methylidene-1,3-dioxolanes from γ-alkoxy-γ-diazo-β-ketoestersen_US
dc.typeArticleen_US
dc.identifier.emailChe, CM:cmche@hku.hken_US
dc.identifier.authorityChe, CM=rp00670en_US
dc.description.naturelink_to_subscribed_fulltexten_US
dc.identifier.doi10.1021/ol010283fen_US
dc.identifier.pmid11893178-
dc.identifier.scopuseid_2-s2.0-0001080627en_US
dc.identifier.hkuros72397-
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-0001080627&selection=ref&src=s&origin=recordpageen_US
dc.identifier.volume4en_US
dc.identifier.issue6en_US
dc.identifier.spage889en_US
dc.identifier.epage892en_US
dc.identifier.isiWOS:000174441700006-
dc.publisher.placeUnited Statesen_US
dc.identifier.scopusauthoridZheng, SL=7403146353en_US
dc.identifier.scopusauthoridYu, WY=7403913673en_US
dc.identifier.scopusauthoridChe, CM=7102442791en_US

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