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Article: A cyclodextrin-modified ketoester for stereoselective epoxidation of alkenes

TitleA cyclodextrin-modified ketoester for stereoselective epoxidation of alkenes
Authors
Issue Date2003
PublisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/joc
Citation
Journal Of Organic Chemistry, 2003, v. 68 n. 17, p. 6576-6582 How to Cite?
AbstractA β-cyclodextrin-modified ketoester 2 was prepared by covalent attachment of a reactive ketone moiety to β-cyclodextrin. Treatment of 2 with Oxone as terminal oxidant would produce CD-substituted dioxirane, which can effect stereoselective alkene epoxidation. The 2-mediated (S)-α-terpineol epoxidations proceeded to give terpineol oxides in high yields, and the stereoselectivities (i.e., cis-/trans-epoxide ratio) decreased from 2.5:1 to 1:1.2 with increasing steric bulkiness of the terpenes. This steric-dependent stereoselectivity can be understood based on different binding geometries of the 2/terpene inclusion complexes according to the 1H NMR titration and 2D ROESY experiments. Enantioselective epoxidation of styrenes has also been achieved with 2 as catalyst (20-50 mol %) in aqueous acetonitrile solution, and up to 40% ee was obtained in 4-chlorostyrene epoxidation at 0 °C. Similar enantioselectivities were also obtained for the 2-mediated epoxidation of 1,2-dihydronaphthalene (37% ee), 4-chlorostyrene (36% ee), and trans-stilbene (31% ee).
Persistent Identifierhttp://hdl.handle.net/10722/69009
ISSN
2015 Impact Factor: 4.785
2015 SCImago Journal Rankings: 2.095
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorChan, WKen_HK
dc.contributor.authorYu, WYen_HK
dc.contributor.authorChe, CMen_HK
dc.contributor.authorWong, MKen_HK
dc.date.accessioned2010-09-06T06:09:43Z-
dc.date.available2010-09-06T06:09:43Z-
dc.date.issued2003en_HK
dc.identifier.citationJournal Of Organic Chemistry, 2003, v. 68 n. 17, p. 6576-6582en_HK
dc.identifier.issn0022-3263en_HK
dc.identifier.urihttp://hdl.handle.net/10722/69009-
dc.description.abstractA β-cyclodextrin-modified ketoester 2 was prepared by covalent attachment of a reactive ketone moiety to β-cyclodextrin. Treatment of 2 with Oxone as terminal oxidant would produce CD-substituted dioxirane, which can effect stereoselective alkene epoxidation. The 2-mediated (S)-α-terpineol epoxidations proceeded to give terpineol oxides in high yields, and the stereoselectivities (i.e., cis-/trans-epoxide ratio) decreased from 2.5:1 to 1:1.2 with increasing steric bulkiness of the terpenes. This steric-dependent stereoselectivity can be understood based on different binding geometries of the 2/terpene inclusion complexes according to the 1H NMR titration and 2D ROESY experiments. Enantioselective epoxidation of styrenes has also been achieved with 2 as catalyst (20-50 mol %) in aqueous acetonitrile solution, and up to 40% ee was obtained in 4-chlorostyrene epoxidation at 0 °C. Similar enantioselectivities were also obtained for the 2-mediated epoxidation of 1,2-dihydronaphthalene (37% ee), 4-chlorostyrene (36% ee), and trans-stilbene (31% ee).en_HK
dc.languageengen_HK
dc.publisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/jocen_HK
dc.relation.ispartofJournal of Organic Chemistryen_HK
dc.titleA cyclodextrin-modified ketoester for stereoselective epoxidation of alkenesen_HK
dc.typeArticleen_HK
dc.identifier.openurlhttp://library.hku.hk:4550/resserv?sid=HKU:IR&issn=0022-3263&volume=68&spage=6576&epage=6582&date=2003&atitle=A+cyclodextrin-modified+ketoester+for+stereoselective+epoxidation+of+alkenesen_HK
dc.identifier.emailChe, CM:cmche@hku.hken_HK
dc.identifier.authorityChe, CM=rp00670en_HK
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1021/jo034296den_HK
dc.identifier.pmid12919018-
dc.identifier.scopuseid_2-s2.0-0042009333en_HK
dc.identifier.hkuros91408en_HK
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-0042009333&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume68en_HK
dc.identifier.issue17en_HK
dc.identifier.spage6576en_HK
dc.identifier.epage6582en_HK
dc.identifier.isiWOS:000184833500013-
dc.publisher.placeUnited Statesen_HK
dc.identifier.scopusauthoridChan, WK=36545712200en_HK
dc.identifier.scopusauthoridYu, WY=7403913673en_HK
dc.identifier.scopusauthoridChe, CM=7102442791en_HK
dc.identifier.scopusauthoridWong, MK=7403908449en_HK

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