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Article: Copper(I)-catalyzed asymmetric alkene aziridination mediated by PhI(OAc)2: A facile one-pot procedure

TitleCopper(I)-catalyzed asymmetric alkene aziridination mediated by PhI(OAc)2: A facile one-pot procedure
Authors
Kwong, HLLiu, DChan, KYLee, CSHuang, KHChe, CM
KeywordsCopper catalyst
Iodobenzene diacetate
One-pot asymmetric aziridination
Styrene
Sulfonamides
Issue Date2004
PublisherPergamon. The Journal's web site is located at http://www.elsevier.com/locate/tetlet
Citation
Tetrahedron Letters, 2004, v. 45 n. 20, p. 3965-3968 How to Cite?
DOI: http://dx.doi.org/10.1016/j.tetlet.2004.03.107
AbstractA facile one-pot procedure for copper-catalyzed PhI(OAc) 2-mediated asymmetric alkene aziridination had been developed. Commercially available PhI(OAc)2 and sulfonamides were used to generate the nitrene precursors (PhI=NR) in situ for olefin aziridination. This one-pot procedure had been optimized using 4-nitrobenzenesulfonamide as the nitrene source. With 5mol% of the chiral copper catalyst, these conditions afforded 94% yield of the isolated product with 75% ee. We had also developed a simple and rapid method to monitor the rate of this one-pot aziridination. © 2004 Elsevier Ltd. All rights reserved.
Persistent Identifierhttp://hdl.handle.net/10722/70116
ISSN
0040-4039
2023 Impact Factor: 1.5
2023 SCImago Journal Rankings: 0.323
ISI Accession Number ID
WOS:000221201900028
References
References in Scopus

 

DC FieldValueLanguage
dc.contributor.authorKwong, HLen_HK
dc.contributor.authorLiu, Den_HK
dc.contributor.authorChan, KYen_HK
dc.contributor.authorLee, CSen_HK
dc.contributor.authorHuang, KHen_HK
dc.contributor.authorChe, CMen_HK
dc.date.accessioned2010-09-06T06:19:52Z-
dc.date.available2010-09-06T06:19:52Z-
dc.date.issued2004en_HK
dc.identifier.citationTetrahedron Letters, 2004, v. 45 n. 20, p. 3965-3968en_HK
dc.identifier.issn0040-4039en_HK
dc.identifier.urihttp://hdl.handle.net/10722/70116-
dc.description.abstractA facile one-pot procedure for copper-catalyzed PhI(OAc) 2-mediated asymmetric alkene aziridination had been developed. Commercially available PhI(OAc)2 and sulfonamides were used to generate the nitrene precursors (PhI=NR) in situ for olefin aziridination. This one-pot procedure had been optimized using 4-nitrobenzenesulfonamide as the nitrene source. With 5mol% of the chiral copper catalyst, these conditions afforded 94% yield of the isolated product with 75% ee. We had also developed a simple and rapid method to monitor the rate of this one-pot aziridination. © 2004 Elsevier Ltd. All rights reserved.en_HK
dc.languageengen_HK
dc.publisherPergamon. The Journal's web site is located at http://www.elsevier.com/locate/tetleten_HK
dc.relation.ispartofTetrahedron Lettersen_HK
dc.subjectCopper catalysten_HK
dc.subjectIodobenzene diacetateen_HK
dc.subjectOne-pot asymmetric aziridinationen_HK
dc.subjectStyreneen_HK
dc.subjectSulfonamidesen_HK
dc.titleCopper(I)-catalyzed asymmetric alkene aziridination mediated by PhI(OAc)2: A facile one-pot procedureen_HK
dc.typeArticleen_HK
dc.identifier.openurlhttp://library.hku.hk:4550/resserv?sid=HKU:IR&issn=0040-4039&volume=45&spage=3965&epage=3968&date=2004&atitle=Copper(I)-catalyzed+asymmetric+alkene+aziridination+mediated+by+PhI(OAc)2:+a+facile+one-pot+procedureen_HK
dc.identifier.emailChe, CM:cmche@hku.hken_HK
dc.identifier.authorityChe, CM=rp00670en_HK
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1016/j.tetlet.2004.03.107en_HK
dc.identifier.scopuseid_2-s2.0-1942504284en_HK
dc.identifier.hkuros94191en_HK
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-1942504284&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume45en_HK
dc.identifier.issue20en_HK
dc.identifier.spage3965en_HK
dc.identifier.epage3968en_HK
dc.identifier.isiWOS:000221201900028-
dc.publisher.placeUnited Kingdomen_HK
dc.identifier.scopusauthoridKwong, HL=35569416300en_HK
dc.identifier.scopusauthoridLiu, D=8891605500en_HK
dc.identifier.scopusauthoridChan, KY=36915709900en_HK
dc.identifier.scopusauthoridLee, CS=35201187300en_HK
dc.identifier.scopusauthoridHuang, KH=7403187706en_HK
dc.identifier.scopusauthoridChe, CM=7102442791en_HK
dc.identifier.issnl0040-4039-

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