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Article: Selective approach toward multifunctionalized lactams by lewis acid promoted PhSe group transfer radical cyclization

TitleSelective approach toward multifunctionalized lactams by lewis acid promoted PhSe group transfer radical cyclization
Authors
Issue Date2010
PublisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/joc
Citation
Journal Of Organic Chemistry, 2010, v. 75 n. 10, p. 3232-3239 How to Cite?
AbstractWe have developed a regiospecific and highly stereoselective strategy for constructing the five-/six-membered monocyclic and bicyclic nitrogen heterocycle skeletons using PhSe group transfer radical cyclization of α-phenylseleno amido esters promoted by a Lewis acid (e.g., Yb(OTf) 3) under UV irradiation. We obtained 5-/6-exo-trig mode cyclization products for the N-allyl/homoallyl substrates, whereas the enamide substrate gave 5-endo-trig ring closure. © 2010 American Chemical Society.
Persistent Identifierhttp://hdl.handle.net/10722/168457
ISSN
2015 Impact Factor: 4.785
2015 SCImago Journal Rankings: 2.095
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorYu, JDen_US
dc.contributor.authorDing, Wen_US
dc.contributor.authorLian, GYen_US
dc.contributor.authorSong, KSen_US
dc.contributor.authorZhang, DWen_US
dc.contributor.authorGao, Xen_US
dc.contributor.authorYang, Den_US
dc.date.accessioned2012-10-08T03:19:09Z-
dc.date.available2012-10-08T03:19:09Z-
dc.date.issued2010en_US
dc.identifier.citationJournal Of Organic Chemistry, 2010, v. 75 n. 10, p. 3232-3239en_US
dc.identifier.issn0022-3263en_US
dc.identifier.urihttp://hdl.handle.net/10722/168457-
dc.description.abstractWe have developed a regiospecific and highly stereoselective strategy for constructing the five-/six-membered monocyclic and bicyclic nitrogen heterocycle skeletons using PhSe group transfer radical cyclization of α-phenylseleno amido esters promoted by a Lewis acid (e.g., Yb(OTf) 3) under UV irradiation. We obtained 5-/6-exo-trig mode cyclization products for the N-allyl/homoallyl substrates, whereas the enamide substrate gave 5-endo-trig ring closure. © 2010 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.meshCyclizationen_US
dc.subject.meshFree Radicals - Chemical Synthesis - Chemistryen_US
dc.subject.meshLactams - Chemical Synthesis - Chemistryen_US
dc.subject.meshMesylates - Chemistryen_US
dc.subject.meshMolecular Structureen_US
dc.subject.meshOrganometallic Compounds - Chemistryen_US
dc.subject.meshOrganoselenium Compounds - Chemistryen_US
dc.subject.meshStereoisomerismen_US
dc.subject.meshUltraviolet Raysen_US
dc.titleSelective approach toward multifunctionalized lactams by lewis acid promoted PhSe group transfer radical cyclizationen_US
dc.typeArticleen_US
dc.identifier.emailYang, D:yangdan@hku.hken_US
dc.identifier.authorityYang, D=rp00825en_US
dc.description.naturelink_to_subscribed_fulltexten_US
dc.identifier.doi10.1021/jo100139uen_US
dc.identifier.pmid20405934-
dc.identifier.scopuseid_2-s2.0-77952537954en_US
dc.identifier.hkuros180946-
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-77952537954&selection=ref&src=s&origin=recordpageen_US
dc.identifier.volume75en_US
dc.identifier.issue10en_US
dc.identifier.spage3232en_US
dc.identifier.epage3239en_US
dc.identifier.isiWOS:000277531200008-
dc.publisher.placeUnited Statesen_US
dc.identifier.scopusauthoridYu, JD=16200500400en_US
dc.identifier.scopusauthoridDing, W=35964344800en_US
dc.identifier.scopusauthoridLian, GY=14026717700en_US
dc.identifier.scopusauthoridSong, KS=7401740599en_US
dc.identifier.scopusauthoridZhang, DW=35320759400en_US
dc.identifier.scopusauthoridGao, X=8084284600en_US
dc.identifier.scopusauthoridYang, D=7404800756en_US

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