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Article: Asymmetric inter- and intramolecular cyclopropanations of alkenes catalyzed by rhodium D4-porphyrin: A comparison of rhodium- and ruthenium-centred catalysts

TitleAsymmetric inter- and intramolecular cyclopropanations of alkenes catalyzed by rhodium D4-porphyrin: A comparison of rhodium- and ruthenium-centred catalysts
Authors
Issue Date2003
PublisherPergamon. The Journal's web site is located at http://www.elsevier.com/locate/tetasy
Citation
Tetrahedron Asymmetry, 2003, v. 14 n. 7, p. 837-844 How to Cite?
AbstractIodo-(5,10,15,20-tetrakis(1,2,3,4,5,6,7,8-octahydro-1,4:5,8- dimethanoanthracen-9-yl)porphyrinatorhodium(III), designated as [Rh(P*)(I)], was prepared and its catalytic activity in the asymmetric cyclopropanation of alkenes with ethyl diazoacetate (EDA) was examined. High catalyst turnovers (TON >103) and moderate enantioselectivities (up to 68% ee) were observed. However, the obtained trans/cis ratios are low. Competition experiments revealed that electron-donating substituents on styrene accelerate the cyclopropanations. The log(kX/kH) versus σ+ plot for substituted styrenes exhibits a good linearity with a small negative ρ+ value (-0.14). [Rh(P*)(I)] is also active in the intramolecular cyclopropanation of allyl diazoacetates. A comparison between rhodium and ruthenium porphyrin complexes was made. © 2003 Elsevier Science Ltd. All rights reserved.
Persistent Identifierhttp://hdl.handle.net/10722/68906
ISSN
2015 Impact Factor: 2.108
2015 SCImago Journal Rankings: 0.806
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorTeng, PFen_HK
dc.contributor.authorLai, TSen_HK
dc.contributor.authorKwong, HLen_HK
dc.contributor.authorChe, CMen_HK
dc.date.accessioned2010-09-06T06:08:48Z-
dc.date.available2010-09-06T06:08:48Z-
dc.date.issued2003en_HK
dc.identifier.citationTetrahedron Asymmetry, 2003, v. 14 n. 7, p. 837-844en_HK
dc.identifier.issn0957-4166en_HK
dc.identifier.urihttp://hdl.handle.net/10722/68906-
dc.description.abstractIodo-(5,10,15,20-tetrakis(1,2,3,4,5,6,7,8-octahydro-1,4:5,8- dimethanoanthracen-9-yl)porphyrinatorhodium(III), designated as [Rh(P*)(I)], was prepared and its catalytic activity in the asymmetric cyclopropanation of alkenes with ethyl diazoacetate (EDA) was examined. High catalyst turnovers (TON >103) and moderate enantioselectivities (up to 68% ee) were observed. However, the obtained trans/cis ratios are low. Competition experiments revealed that electron-donating substituents on styrene accelerate the cyclopropanations. The log(kX/kH) versus σ+ plot for substituted styrenes exhibits a good linearity with a small negative ρ+ value (-0.14). [Rh(P*)(I)] is also active in the intramolecular cyclopropanation of allyl diazoacetates. A comparison between rhodium and ruthenium porphyrin complexes was made. © 2003 Elsevier Science Ltd. All rights reserved.en_HK
dc.languageengen_HK
dc.publisherPergamon. The Journal's web site is located at http://www.elsevier.com/locate/tetasyen_HK
dc.relation.ispartofTetrahedron Asymmetryen_HK
dc.titleAsymmetric inter- and intramolecular cyclopropanations of alkenes catalyzed by rhodium D4-porphyrin: A comparison of rhodium- and ruthenium-centred catalystsen_HK
dc.typeArticleen_HK
dc.identifier.openurlhttp://library.hku.hk:4550/resserv?sid=HKU:IR&issn=0957-4166&volume=14&spage=837&epage=844&date=2003&atitle=Asymmetric+inter-+and+intramolecular+cyclopropanations+of+alkenes+catalyzed+by+rhodium+D4-porphyrin:++a+comparison+of+rhodium-+and+ruthenium-centred+catalystsen_HK
dc.identifier.emailChe, CM:cmche@hku.hken_HK
dc.identifier.authorityChe, CM=rp00670en_HK
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1016/S0957-4166(03)00047-8en_HK
dc.identifier.scopuseid_2-s2.0-0037418803en_HK
dc.identifier.hkuros83828en_HK
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-0037418803&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume14en_HK
dc.identifier.issue7en_HK
dc.identifier.spage837en_HK
dc.identifier.epage844en_HK
dc.identifier.isiWOS:000182150200009-
dc.publisher.placeUnited Kingdomen_HK
dc.identifier.scopusauthoridTeng, PF=7006192221en_HK
dc.identifier.scopusauthoridLai, TS=7202203490en_HK
dc.identifier.scopusauthoridKwong, HL=35569416300en_HK
dc.identifier.scopusauthoridChe, CM=7102442791en_HK

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