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Article: Metalloporphyrin-catalyzed diastereoselective epoxidation of allyl-substituted alkenes

TitleMetalloporphyrin-catalyzed diastereoselective epoxidation of allyl-substituted alkenes
Authors
Chan, WKWong, MKChe, CM
Issue Date2005
PublisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/joc
Citation
Journal Of Organic Chemistry, 2005, v. 70 n. 11, p. 4226-4232 How to Cite?
DOI: http://dx.doi.org/10.1021/jo047733c
AbstractBy using [Mn(2,6-Cl2TPP)Cl] (1) as a catalyst and Oxone/H 2O2 as an oxidant, we have developed an efficient method for erythro-selective epoxidation of acyclic allyl-substituted alkenes, including allylic alcohols, amines, and esters. Up to 9:1 erythro selectivities for terminal allyllic alkenes could be achieved, which are significantly higher than that achieved using m-CPBA as an oxidant. In addition, the synthetic utilities of this epoxidation method were highlighted in stereoselective synthesis of key anti-HIV drug intermediates and epoxidation of glycals. © 2005 American Chemical Society.
Persistent Identifierhttp://hdl.handle.net/10722/167927
ISSN
0022-3263
2021 Impact Factor: 4.198
2020 SCImago Journal Rankings: 1.200
ISI Accession Number ID
WOS:000229321100002
References
References in Scopus

 

DC FieldValueLanguage
dc.contributor.authorChan, WKen_US
dc.contributor.authorWong, MKen_US
dc.contributor.authorChe, CMen_US
dc.date.accessioned2012-10-08T03:13:02Z-
dc.date.available2012-10-08T03:13:02Z-
dc.date.issued2005en_US
dc.identifier.citationJournal Of Organic Chemistry, 2005, v. 70 n. 11, p. 4226-4232en_US
dc.identifier.issn0022-3263en_US
dc.identifier.urihttp://hdl.handle.net/10722/167927-
dc.description.abstractBy using [Mn(2,6-Cl2TPP)Cl] (1) as a catalyst and Oxone/H 2O2 as an oxidant, we have developed an efficient method for erythro-selective epoxidation of acyclic allyl-substituted alkenes, including allylic alcohols, amines, and esters. Up to 9:1 erythro selectivities for terminal allyllic alkenes could be achieved, which are significantly higher than that achieved using m-CPBA as an oxidant. In addition, the synthetic utilities of this epoxidation method were highlighted in stereoselective synthesis of key anti-HIV drug intermediates and epoxidation of glycals. © 2005 American Chemical Society.en_US
dc.languageengen_US
dc.publisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/jocen_US
dc.relation.ispartofJournal of Organic Chemistryen_US
dc.subject.meshAlkenes - Chemistryen_US
dc.subject.meshAnti-Hiv Agents - Chemistryen_US
dc.subject.meshCatalysisen_US
dc.subject.meshEpoxy Compounds - Chemical Synthesisen_US
dc.subject.meshManganese - Chemistryen_US
dc.subject.meshMetalloporphyrins - Chemistryen_US
dc.subject.meshModels, Molecularen_US
dc.subject.meshMolecular Structureen_US
dc.subject.meshOrganometallic Compounds - Chemistryen_US
dc.subject.meshOxidants - Chemistryen_US
dc.subject.meshOxidation-Reductionen_US
dc.subject.meshStereoisomerismen_US
dc.titleMetalloporphyrin-catalyzed diastereoselective epoxidation of allyl-substituted alkenesen_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.doi10.1021/jo047733cen_US
dc.identifier.pmid15903294-
dc.identifier.scopuseid_2-s2.0-19544375784en_US
dc.identifier.hkuros100038-
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-19544375784&selection=ref&src=s&origin=recordpageen_US
dc.identifier.volume70en_US
dc.identifier.issue11en_US
dc.identifier.spage4226en_US
dc.identifier.epage4232en_US
dc.identifier.isiWOS:000229321100002-
dc.publisher.placeUnited Statesen_US
dc.identifier.scopusauthoridChan, WK=36545712200en_US
dc.identifier.scopusauthoridWong, MK=7403908449en_US
dc.identifier.scopusauthoridChe, CM=7102442791en_US
dc.identifier.issnl0022-3263-

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