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- Publisher Website: 10.1021/jo100139u
- Scopus: eid_2-s2.0-77952537954
- PMID: 20405934
- WOS: WOS:000277531200008
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Article: Selective approach toward multifunctionalized lactams by lewis acid promoted PhSe group transfer radical cyclization
Title | Selective approach toward multifunctionalized lactams by lewis acid promoted PhSe group transfer radical cyclization |
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Authors | |
Issue Date | 2010 |
Publisher | American 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? |
Abstract | We 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 Identifier | http://hdl.handle.net/10722/168457 |
ISSN | 2023 Impact Factor: 3.3 2023 SCImago Journal Rankings: 0.724 |
ISI Accession Number ID | |
References |
DC Field | Value | Language |
---|---|---|
dc.contributor.author | Yu, JD | en_US |
dc.contributor.author | Ding, W | en_US |
dc.contributor.author | Lian, GY | en_US |
dc.contributor.author | Song, KS | en_US |
dc.contributor.author | Zhang, DW | en_US |
dc.contributor.author | Gao, X | en_US |
dc.contributor.author | Yang, D | en_US |
dc.date.accessioned | 2012-10-08T03:19:09Z | - |
dc.date.available | 2012-10-08T03:19:09Z | - |
dc.date.issued | 2010 | en_US |
dc.identifier.citation | Journal Of Organic Chemistry, 2010, v. 75 n. 10, p. 3232-3239 | en_US |
dc.identifier.issn | 0022-3263 | en_US |
dc.identifier.uri | http://hdl.handle.net/10722/168457 | - |
dc.description.abstract | We 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.language | eng | en_US |
dc.publisher | American Chemical Society. The Journal's web site is located at http://pubs.acs.org/joc | en_US |
dc.relation.ispartof | Journal of Organic Chemistry | en_US |
dc.subject.mesh | Cyclization | en_US |
dc.subject.mesh | Free Radicals - Chemical Synthesis - Chemistry | en_US |
dc.subject.mesh | Lactams - Chemical Synthesis - Chemistry | en_US |
dc.subject.mesh | Mesylates - Chemistry | en_US |
dc.subject.mesh | Molecular Structure | en_US |
dc.subject.mesh | Organometallic Compounds - Chemistry | en_US |
dc.subject.mesh | Organoselenium Compounds - Chemistry | en_US |
dc.subject.mesh | Stereoisomerism | en_US |
dc.subject.mesh | Ultraviolet Rays | en_US |
dc.title | Selective approach toward multifunctionalized lactams by lewis acid promoted PhSe group transfer radical cyclization | en_US |
dc.type | Article | en_US |
dc.identifier.email | Yang, D:yangdan@hku.hk | en_US |
dc.identifier.authority | Yang, D=rp00825 | en_US |
dc.description.nature | link_to_subscribed_fulltext | en_US |
dc.identifier.doi | 10.1021/jo100139u | en_US |
dc.identifier.pmid | 20405934 | - |
dc.identifier.scopus | eid_2-s2.0-77952537954 | en_US |
dc.identifier.hkuros | 180946 | - |
dc.relation.references | http://www.scopus.com/mlt/select.url?eid=2-s2.0-77952537954&selection=ref&src=s&origin=recordpage | en_US |
dc.identifier.volume | 75 | en_US |
dc.identifier.issue | 10 | en_US |
dc.identifier.spage | 3232 | en_US |
dc.identifier.epage | 3239 | en_US |
dc.identifier.isi | WOS:000277531200008 | - |
dc.publisher.place | United States | en_US |
dc.identifier.scopusauthorid | Yu, JD=16200500400 | en_US |
dc.identifier.scopusauthorid | Ding, W=35964344800 | en_US |
dc.identifier.scopusauthorid | Lian, GY=14026717700 | en_US |
dc.identifier.scopusauthorid | Song, KS=7401740599 | en_US |
dc.identifier.scopusauthorid | Zhang, DW=35320759400 | en_US |
dc.identifier.scopusauthorid | Gao, X=8084284600 | en_US |
dc.identifier.scopusauthorid | Yang, D=7404800756 | en_US |
dc.identifier.issnl | 0022-3263 | - |