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Article: Enantioselective epoxidation of trans-disubstituted alkenes by D2-symmetric chiral dioxoruthenium(VI) porphyrins
Title | Enantioselective epoxidation of trans-disubstituted alkenes by D2-symmetric chiral dioxoruthenium(VI) porphyrins |
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Authors | |
Issue Date | 1999 |
Publisher | American 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? |
Abstract | A 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 Identifier | http://hdl.handle.net/10722/167619 |
ISSN |
DC Field | Value | Language |
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dc.contributor.author | Zhang, R | en_US |
dc.contributor.author | Yu, WY | en_US |
dc.contributor.author | Lai, TS | en_US |
dc.contributor.author | Che, CM | en_US |
dc.date.accessioned | 2012-10-08T03:09:08Z | - |
dc.date.available | 2012-10-08T03:09:08Z | - |
dc.date.issued | 1999 | en_US |
dc.identifier.citation | Acs National Meeting Book Of Abstracts, 1999, v. PART 1, p. INOR-69 | en_US |
dc.identifier.issn | 0065-7727 | en_US |
dc.identifier.uri | http://hdl.handle.net/10722/167619 | - |
dc.description.abstract | A 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.language | eng | en_US |
dc.publisher | American Chemical Society. The Journal's web site is located at http://www.chemistry.org/portal/a/c/s/1/acsdisplay.html?DOC=meetingspast.html | en_US |
dc.relation.ispartof | ACS National Meeting Book of Abstracts | en_US |
dc.title | Enantioselective epoxidation of trans-disubstituted alkenes by D2-symmetric chiral dioxoruthenium(VI) porphyrins | en_US |
dc.type | Article | en_US |
dc.identifier.email | Che, CM:cmche@hku.hk | en_US |
dc.identifier.authority | Che, CM=rp00670 | en_US |
dc.description.nature | link_to_subscribed_fulltext | en_US |
dc.identifier.scopus | eid_2-s2.0-0033369403 | en_US |
dc.identifier.volume | PART 1 | en_US |
dc.identifier.spage | INOR | en_US |
dc.identifier.epage | 69 | en_US |
dc.publisher.place | United States | en_US |
dc.identifier.scopusauthorid | Zhang, R=7404865969 | en_US |
dc.identifier.scopusauthorid | Yu, WY=7403913673 | en_US |
dc.identifier.scopusauthorid | Lai, TS=7202203490 | en_US |
dc.identifier.scopusauthorid | Che, CM=7102442791 | en_US |
dc.identifier.issnl | 0065-7727 | - |