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Article: Lewis acid-catalyzed atom transfer radical cyclization of unsaturated β-keto amides

TitleLewis acid-catalyzed atom transfer radical cyclization of unsaturated β-keto amides
Authors
Yang, DYan, YLLaw, KLZhu, NY
KeywordsKeto amide
Lewis acid
Radical cyclization
Issue Date2003
PublisherPergamon. The Journal's web site is located at http://www.elsevier.com/locate/tet
Citation
Tetrahedron, 2003, v. 59 n. 52, p. 10465-10475 How to Cite?
DOI: http://dx.doi.org/10.1016/j.tet.2003.06.009
AbstractThe Lewis acid-catalyzed atom transfer radical cyclization reactions of olefinic α-bromo β-keto amides were investigated. It was found Lewis acid Yb(OTf) 3 or Mg(ClO 4) 2 not only promoted the cyclization reactions, but also resulted in excellent trans stereocontrol in the cyclization products. With the catalysis of Lewis acid Yb(OTf) 3 or Mg(ClO 4) 2 at -78°C in the presence of Et 3B/O 2, the cyclization reactions of C-olefinic β-keto amides provided cyclic ketones, while the cyclization reactions of N-olefinic β-keto amides led to the formation of γ-lactams, which could be converted to 3-aza-bicyclo[3,1,0]hexan-2-ones. © 2003 Elsevier Ltd. All rights reserved.
Persistent Identifierhttp://hdl.handle.net/10722/167867
ISSN
0040-4020
2023 Impact Factor: 2.1
2023 SCImago Journal Rankings: 0.406
ISI Accession Number ID
WOS:000187357800012
References
References in Scopus

 

DC FieldValueLanguage
dc.contributor.authorYang, Den_HK
dc.contributor.authorYan, YLen_HK
dc.contributor.authorLaw, KLen_HK
dc.contributor.authorZhu, NYen_HK
dc.date.accessioned2012-10-08T03:12:20Z-
dc.date.available2012-10-08T03:12:20Z-
dc.date.issued2003en_HK
dc.identifier.citationTetrahedron, 2003, v. 59 n. 52, p. 10465-10475en_HK
dc.identifier.issn0040-4020en_HK
dc.identifier.urihttp://hdl.handle.net/10722/167867-
dc.description.abstractThe Lewis acid-catalyzed atom transfer radical cyclization reactions of olefinic α-bromo β-keto amides were investigated. It was found Lewis acid Yb(OTf) 3 or Mg(ClO 4) 2 not only promoted the cyclization reactions, but also resulted in excellent trans stereocontrol in the cyclization products. With the catalysis of Lewis acid Yb(OTf) 3 or Mg(ClO 4) 2 at -78°C in the presence of Et 3B/O 2, the cyclization reactions of C-olefinic β-keto amides provided cyclic ketones, while the cyclization reactions of N-olefinic β-keto amides led to the formation of γ-lactams, which could be converted to 3-aza-bicyclo[3,1,0]hexan-2-ones. © 2003 Elsevier Ltd. All rights reserved.en_HK
dc.languageengen_US
dc.publisherPergamon. The Journal's web site is located at http://www.elsevier.com/locate/teten_HK
dc.relation.ispartofTetrahedronen_HK
dc.subjectKeto amideen_HK
dc.subjectLewis aciden_HK
dc.subjectRadical cyclizationen_HK
dc.titleLewis acid-catalyzed atom transfer radical cyclization of unsaturated β-keto amidesen_HK
dc.typeArticleen_HK
dc.identifier.emailYang, D: yangdan@hku.hken_HK
dc.identifier.emailZhu, NY: nzhu@hkucc.hku.hken_HK
dc.identifier.authorityYang, D=rp00825en_HK
dc.identifier.authorityZhu, NY=rp00845en_HK
dc.description.naturelink_to_subscribed_fulltexten_US
dc.identifier.doi10.1016/j.tet.2003.06.009en_HK
dc.identifier.scopuseid_2-s2.0-0348050031en_HK
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-0348050031&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume59en_HK
dc.identifier.issue52en_HK
dc.identifier.spage10465en_HK
dc.identifier.epage10475en_HK
dc.identifier.isiWOS:000187357800012-
dc.publisher.placeUnited Kingdomen_HK
dc.identifier.scopusauthoridYang, D=7404800756en_HK
dc.identifier.scopusauthoridYan, YL=7404586174en_HK
dc.identifier.scopusauthoridLaw, KL=7202563094en_HK
dc.identifier.scopusauthoridZhu, NY=7201449530en_HK
dc.identifier.issnl0040-4020-

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