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Article: Synthesis of γ-butyrolactams by photoinduced PhSe group transfer radical cyclization and formal synthesis of (±)-isocynometrine with diphenyldiselenide as promoter

TitleSynthesis of γ-butyrolactams by photoinduced PhSe group transfer radical cyclization and formal synthesis of (±)-isocynometrine with diphenyldiselenide as promoter
Authors
Issue Date2009
PublisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/joc
Citation
Journal Of Organic Chemistry, 2009, v. 74 n. 22, p. 8610-8615 How to Cite?
Abstract(Chemical Equation Presented) We have developed a strategy for constructing nitrogen heterocycles by photoinduced PhSe group transfer radical cyclization. trans-α,β-Disubstituted γ-butyrolactams (2-pyrrolidinones) were prepared in good yields (38-73%) with high regioselectivity and stereoselectivity from N-alkenyl α-PhSe β-keto amides. Reaction outcomes were modulated by the steric effect of the substituents on the nitrogen atom of the cyclization precursors and the stereoelectronic effect of the substrates. Diphenyldiselenide, as an additive, was found to promote ring closure. The advantage of this strategy in natural product synthesis is demonstrated by a formal synthesis of (±)-isocynometrine. © 2009 American Chemical Society.
Persistent Identifierhttp://hdl.handle.net/10722/168415
ISSN
2015 Impact Factor: 4.785
2015 SCImago Journal Rankings: 2.095
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorYang, Den_US
dc.contributor.authorLian, GYen_US
dc.contributor.authorYang, HFen_US
dc.contributor.authorYu, JDen_US
dc.contributor.authorZhang, DWen_US
dc.contributor.authorGao, Xen_US
dc.date.accessioned2012-10-08T03:18:40Z-
dc.date.available2012-10-08T03:18:40Z-
dc.date.issued2009en_US
dc.identifier.citationJournal Of Organic Chemistry, 2009, v. 74 n. 22, p. 8610-8615en_US
dc.identifier.issn0022-3263en_US
dc.identifier.urihttp://hdl.handle.net/10722/168415-
dc.description.abstract(Chemical Equation Presented) We have developed a strategy for constructing nitrogen heterocycles by photoinduced PhSe group transfer radical cyclization. trans-α,β-Disubstituted γ-butyrolactams (2-pyrrolidinones) were prepared in good yields (38-73%) with high regioselectivity and stereoselectivity from N-alkenyl α-PhSe β-keto amides. Reaction outcomes were modulated by the steric effect of the substituents on the nitrogen atom of the cyclization precursors and the stereoelectronic effect of the substrates. Diphenyldiselenide, as an additive, was found to promote ring closure. The advantage of this strategy in natural product synthesis is demonstrated by a formal synthesis of (±)-isocynometrine. © 2009 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.mesh4-Butyrolactone - Analogs & Derivatives - Chemical Synthesis - Chemistryen_US
dc.subject.meshAlkaloids - Chemical Synthesis - Chemistryen_US
dc.subject.meshCyclizationen_US
dc.subject.meshFree Radicals - Chemistryen_US
dc.subject.meshImidazoles - Chemical Synthesis - Chemistryen_US
dc.subject.meshMolecular Structureen_US
dc.subject.meshOrganoselenium Compounds - Chemistryen_US
dc.subject.meshPhotochemistryen_US
dc.subject.meshStereoisomerismen_US
dc.titleSynthesis of γ-butyrolactams by photoinduced PhSe group transfer radical cyclization and formal synthesis of (±)-isocynometrine with diphenyldiselenide as promoteren_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/jo9017099en_US
dc.identifier.pmid19852460-
dc.identifier.scopuseid_2-s2.0-70449652098en_US
dc.identifier.hkuros180940-
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-70449652098&selection=ref&src=s&origin=recordpageen_US
dc.identifier.volume74en_US
dc.identifier.issue22en_US
dc.identifier.spage8610en_US
dc.identifier.epage8615en_US
dc.identifier.isiWOS:000271662500014-
dc.publisher.placeUnited Statesen_US
dc.identifier.scopusauthoridYang, D=7404800756en_US
dc.identifier.scopusauthoridLian, GY=14026717700en_US
dc.identifier.scopusauthoridYang, HF=7406558115en_US
dc.identifier.scopusauthoridYu, JD=16200500400en_US
dc.identifier.scopusauthoridZhang, DW=35320759400en_US
dc.identifier.scopusauthoridGao, X=8084284600en_US

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