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Article: Enantioselective epoxidation of trans-disubstituted alkenes by D2-symmetric chiral dioxoruthenium(VI) porphyrins

TitleEnantioselective epoxidation of trans-disubstituted alkenes by D2-symmetric chiral dioxoruthenium(VI) porphyrins
Authors
Issue Date1999
PublisherAmerican Chemical Society. The Journal's web site is located at http://www.chemistry.org/portal/a/c/s/1/acsdisplay.html?DOC=meetingspast.html
Citation
Acs National Meeting Book Of Abstracts, 1999, v. PART 1, p. INOR-69 How to Cite?
AbstractA series of D2-symmetric chiral trans-dioxoruthenium(VI) porphyrins bifacially encumbered by four threitol units with staggered conformation can react favorably with trans-alkenes in exceptional percentages of enantiomeric excess up to 70% and 76% enantiomeric excess are achieved for the epoxidation of trans-β-methylstyrene and cinnamyl chloride, respectively. Much lower enantioselectivity, however, is obtained for the cis-β-methylstyrene. Oxidation by these complexes exhibits clean pseudo-first-order kinetics. The trans-alkene oxidation gives a higher second-order rate constant k2 compared with that of the analogous cis-isomer. A 'head-on approach' model elucidates the stereoselectivity for the trans-preference oxidation. Original is an abstract.
Persistent Identifierhttp://hdl.handle.net/10722/167619
ISSN

 

DC FieldValueLanguage
dc.contributor.authorZhang, Ren_US
dc.contributor.authorYu, WYen_US
dc.contributor.authorLai, TSen_US
dc.contributor.authorChe, CMen_US
dc.date.accessioned2012-10-08T03:09:08Z-
dc.date.available2012-10-08T03:09:08Z-
dc.date.issued1999en_US
dc.identifier.citationAcs National Meeting Book Of Abstracts, 1999, v. PART 1, p. INOR-69en_US
dc.identifier.issn0065-7727en_US
dc.identifier.urihttp://hdl.handle.net/10722/167619-
dc.description.abstractA series of D2-symmetric chiral trans-dioxoruthenium(VI) porphyrins bifacially encumbered by four threitol units with staggered conformation can react favorably with trans-alkenes in exceptional percentages of enantiomeric excess up to 70% and 76% enantiomeric excess are achieved for the epoxidation of trans-β-methylstyrene and cinnamyl chloride, respectively. Much lower enantioselectivity, however, is obtained for the cis-β-methylstyrene. Oxidation by these complexes exhibits clean pseudo-first-order kinetics. The trans-alkene oxidation gives a higher second-order rate constant k2 compared with that of the analogous cis-isomer. A 'head-on approach' model elucidates the stereoselectivity for the trans-preference oxidation. Original is an abstract.en_US
dc.languageengen_US
dc.publisherAmerican Chemical Society. The Journal's web site is located at http://www.chemistry.org/portal/a/c/s/1/acsdisplay.html?DOC=meetingspast.htmlen_US
dc.relation.ispartofACS National Meeting Book of Abstractsen_US
dc.titleEnantioselective epoxidation of trans-disubstituted alkenes by D2-symmetric chiral dioxoruthenium(VI) porphyrinsen_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.scopuseid_2-s2.0-0033369403en_US
dc.identifier.volumePART 1en_US
dc.identifier.spageINORen_US
dc.identifier.epage69en_US
dc.publisher.placeUnited Statesen_US
dc.identifier.scopusauthoridZhang, R=7404865969en_US
dc.identifier.scopusauthoridYu, WY=7403913673en_US
dc.identifier.scopusauthoridLai, TS=7202203490en_US
dc.identifier.scopusauthoridChe, CM=7102442791en_US

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