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Article: Ruthenium-catalyzed stereoselective intramolecular carbenoid C-H insertion for β- and γ-lactam formations by decomposition of α-diazoacetamides

TitleRuthenium-catalyzed stereoselective intramolecular carbenoid C-H insertion for β- and γ-lactam formations by decomposition of α-diazoacetamides
Authors
Choi, MKWYu, WYChe, CM
Issue Date2005
PublisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/journals/orlef7/index.html
Citation
Organic Letters, 2005, v. 7 n. 6, p. 1081-1084 How to Cite?
DOI: http://dx.doi.org/10.1021/ol050003m
Abstract(Chemical Equation Presented) An operationally simple catalytic system based on [RuCl2(p-cymene)2] was developed for stereoselective cyclization of α-diazoacetamides by intramolecular carbenoid C-H insertion, and β-lactams were produced in excellent yields and >99% cis-stereoselectivity. The Ru-catalyzed reactions can be performed without the need for slow addition of diazo compounds and inert atmosphere. With α-diazoanilides as substrate, the carbenoid insertion was directed selectively to aromatic C-H bond leading to γ-lactam formation (>95% yield). © 2005 American Chemical Society.
Persistent Identifierhttp://hdl.handle.net/10722/167916
ISSN
1523-7060
2021 Impact Factor: 6.072
2020 SCImago Journal Rankings: 1.940
ISI Accession Number ID
WOS:000227621000032
References
References in Scopus

 

DC FieldValueLanguage
dc.contributor.authorChoi, MKWen_US
dc.contributor.authorYu, WYen_US
dc.contributor.authorChe, CMen_US
dc.date.accessioned2012-10-08T03:12:54Z-
dc.date.available2012-10-08T03:12:54Z-
dc.date.issued2005en_US
dc.identifier.citationOrganic Letters, 2005, v. 7 n. 6, p. 1081-1084en_US
dc.identifier.issn1523-7060en_US
dc.identifier.urihttp://hdl.handle.net/10722/167916-
dc.description.abstract(Chemical Equation Presented) An operationally simple catalytic system based on [RuCl2(p-cymene)2] was developed for stereoselective cyclization of α-diazoacetamides by intramolecular carbenoid C-H insertion, and β-lactams were produced in excellent yields and >99% cis-stereoselectivity. The Ru-catalyzed reactions can be performed without the need for slow addition of diazo compounds and inert atmosphere. With α-diazoanilides as substrate, the carbenoid insertion was directed selectively to aromatic C-H bond leading to γ-lactam formation (>95% yield). © 2005 American Chemical Society.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.subject.meshCatalysisen_US
dc.subject.meshCyclizationen_US
dc.subject.meshDiazonium Compounds - Chemistryen_US
dc.subject.meshLactams - Chemical Synthesisen_US
dc.subject.meshMolecular Structureen_US
dc.subject.meshRuthenium - Chemistryen_US
dc.subject.meshStereoisomerismen_US
dc.titleRuthenium-catalyzed stereoselective intramolecular carbenoid C-H insertion for β- and γ-lactam formations by decomposition of α-diazoacetamidesen_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/ol050003men_US
dc.identifier.pmid15760144-
dc.identifier.scopuseid_2-s2.0-18244385976en_US
dc.identifier.hkuros107032-
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-18244385976&selection=ref&src=s&origin=recordpageen_US
dc.identifier.volume7en_US
dc.identifier.issue6en_US
dc.identifier.spage1081en_US
dc.identifier.epage1084en_US
dc.identifier.isiWOS:000227621000032-
dc.publisher.placeUnited Statesen_US
dc.identifier.scopusauthoridChoi, MKW=7402093591en_US
dc.identifier.scopusauthoridYu, WY=7403913673en_US
dc.identifier.scopusauthoridChe, CM=7102442791en_US
dc.identifier.issnl1523-7052-

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