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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
Title | Asymmetric inter- and intramolecular cyclopropanations of alkenes catalyzed by rhodium D4-porphyrin: A comparison of rhodium- and ruthenium-centred catalysts |
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Authors | |
Issue Date | 2003 |
Publisher | Pergamon. 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? |
Abstract | Iodo-(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 Identifier | http://hdl.handle.net/10722/68906 |
ISSN | 2016 Impact Factor: 2.126 2020 SCImago Journal Rankings: 0.396 |
ISI Accession Number ID | |
References |
DC Field | Value | Language |
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dc.contributor.author | Teng, PF | en_HK |
dc.contributor.author | Lai, TS | en_HK |
dc.contributor.author | Kwong, HL | en_HK |
dc.contributor.author | Che, CM | en_HK |
dc.date.accessioned | 2010-09-06T06:08:48Z | - |
dc.date.available | 2010-09-06T06:08:48Z | - |
dc.date.issued | 2003 | en_HK |
dc.identifier.citation | Tetrahedron Asymmetry, 2003, v. 14 n. 7, p. 837-844 | en_HK |
dc.identifier.issn | 0957-4166 | en_HK |
dc.identifier.uri | http://hdl.handle.net/10722/68906 | - |
dc.description.abstract | Iodo-(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.language | eng | en_HK |
dc.publisher | Pergamon. The Journal's web site is located at http://www.elsevier.com/locate/tetasy | en_HK |
dc.relation.ispartof | Tetrahedron Asymmetry | en_HK |
dc.title | Asymmetric inter- and intramolecular cyclopropanations of alkenes catalyzed by rhodium D4-porphyrin: A comparison of rhodium- and ruthenium-centred catalysts | en_HK |
dc.type | Article | en_HK |
dc.identifier.openurl | http://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+catalysts | en_HK |
dc.identifier.email | Che, CM:cmche@hku.hk | en_HK |
dc.identifier.authority | Che, CM=rp00670 | en_HK |
dc.description.nature | link_to_subscribed_fulltext | - |
dc.identifier.doi | 10.1016/S0957-4166(03)00047-8 | en_HK |
dc.identifier.scopus | eid_2-s2.0-0037418803 | en_HK |
dc.identifier.hkuros | 83828 | en_HK |
dc.relation.references | http://www.scopus.com/mlt/select.url?eid=2-s2.0-0037418803&selection=ref&src=s&origin=recordpage | en_HK |
dc.identifier.volume | 14 | en_HK |
dc.identifier.issue | 7 | en_HK |
dc.identifier.spage | 837 | en_HK |
dc.identifier.epage | 844 | en_HK |
dc.identifier.isi | WOS:000182150200009 | - |
dc.publisher.place | United Kingdom | en_HK |
dc.identifier.scopusauthorid | Teng, PF=7006192221 | en_HK |
dc.identifier.scopusauthorid | Lai, TS=7202203490 | en_HK |
dc.identifier.scopusauthorid | Kwong, HL=35569416300 | en_HK |
dc.identifier.scopusauthorid | Che, CM=7102442791 | en_HK |
dc.identifier.issnl | 0957-4166 | - |