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- Publisher Website: 10.1021/jo048322z
- Scopus: eid_2-s2.0-10044246186
- PMID: 15575763
- WOS: WOS:000225550300033
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Article: Et2AlCl-promoted asymmetric phenylseleno group transfer radical cyclization reactions of unsaturated β-hydroxy esters
Title | Et2AlCl-promoted asymmetric phenylseleno group transfer radical cyclization reactions of unsaturated β-hydroxy esters |
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Authors | |
Issue Date | 2004 |
Publisher | American Chemical Society. The Journal's web site is located at http://pubs.acs.org/joc |
Citation | Journal Of Organic Chemistry, 2004, v. 69 n. 25, p. 8821-8828 How to Cite? |
Abstract | We have developed a new method for asymmetric phenylseleno group transfer radical cyclization of unsaturated β-hydroxy esters. Various unsaturated α-phenylseleno β-hydroxy esters underwent radical cyclization in the presence of Et2AlCl in benzene with sunlamp irradiation at 25-30 °C to give mono- and bicyclic group-transferred products in an efficient and highly regioselective and diastereoselective manner. To rationalize the high diastereoselectivities observed in this reaction, we propose a model based on chelation control of the aluminum alkoxides that are formed in situ. We devised a general method to prepare chiral radical precursors from which we obtained highly optically pure mono- and bicyclic group transfer products. The synthetic advantages of this method are demonstrated by our formal total synthesis of (-)-wilforonide. This paper presents the first examples of stereoselective group transfer radical cyclizations that occur via 1,2-asymmetric induction. |
Persistent Identifier | http://hdl.handle.net/10722/167876 |
ISSN | 2023 Impact Factor: 3.3 2023 SCImago Journal Rankings: 0.724 |
ISI Accession Number ID | |
References |
DC Field | Value | Language |
---|---|---|
dc.contributor.author | Yang, D | en_HK |
dc.contributor.author | Gao, Q | en_HK |
dc.contributor.author | Zheng, BF | en_HK |
dc.contributor.author | Zhu, NY | en_HK |
dc.date.accessioned | 2012-10-08T03:12:24Z | - |
dc.date.available | 2012-10-08T03:12:24Z | - |
dc.date.issued | 2004 | en_HK |
dc.identifier.citation | Journal Of Organic Chemistry, 2004, v. 69 n. 25, p. 8821-8828 | en_HK |
dc.identifier.issn | 0022-3263 | en_HK |
dc.identifier.uri | http://hdl.handle.net/10722/167876 | - |
dc.description.abstract | We have developed a new method for asymmetric phenylseleno group transfer radical cyclization of unsaturated β-hydroxy esters. Various unsaturated α-phenylseleno β-hydroxy esters underwent radical cyclization in the presence of Et2AlCl in benzene with sunlamp irradiation at 25-30 °C to give mono- and bicyclic group-transferred products in an efficient and highly regioselective and diastereoselective manner. To rationalize the high diastereoselectivities observed in this reaction, we propose a model based on chelation control of the aluminum alkoxides that are formed in situ. We devised a general method to prepare chiral radical precursors from which we obtained highly optically pure mono- and bicyclic group transfer products. The synthetic advantages of this method are demonstrated by our formal total synthesis of (-)-wilforonide. This paper presents the first examples of stereoselective group transfer radical cyclizations that occur via 1,2-asymmetric induction. | en_HK |
dc.language | eng | en_US |
dc.publisher | American Chemical Society. The Journal's web site is located at http://pubs.acs.org/joc | en_HK |
dc.relation.ispartof | Journal of Organic Chemistry | en_HK |
dc.subject.mesh | Aluminum Compounds - Chemistry | en_US |
dc.subject.mesh | Cyclization | en_US |
dc.subject.mesh | Esters - Chemical Synthesis | en_US |
dc.subject.mesh | Free Radicals - Chemistry | en_US |
dc.subject.mesh | Hydroxy Acids - Chemical Synthesis | en_US |
dc.subject.mesh | Molecular Conformation | en_US |
dc.subject.mesh | Organometallic Compounds - Chemistry | en_US |
dc.subject.mesh | Selenium - Chemistry | en_US |
dc.title | Et2AlCl-promoted asymmetric phenylseleno group transfer radical cyclization reactions of unsaturated β-hydroxy esters | en_HK |
dc.type | Article | en_HK |
dc.identifier.email | Yang, D: yangdan@hku.hk | en_HK |
dc.identifier.email | Zhu, NY: nzhu@hkucc.hku.hk | en_HK |
dc.identifier.authority | Yang, D=rp00825 | en_HK |
dc.identifier.authority | Zhu, NY=rp00845 | en_HK |
dc.description.nature | link_to_subscribed_fulltext | en_US |
dc.identifier.doi | 10.1021/jo048322z | en_HK |
dc.identifier.pmid | 15575763 | - |
dc.identifier.scopus | eid_2-s2.0-10044246186 | en_HK |
dc.identifier.hkuros | 98425 | - |
dc.relation.references | http://www.scopus.com/mlt/select.url?eid=2-s2.0-10044246186&selection=ref&src=s&origin=recordpage | en_HK |
dc.identifier.volume | 69 | en_HK |
dc.identifier.issue | 25 | en_HK |
dc.identifier.spage | 8821 | en_HK |
dc.identifier.epage | 8828 | en_HK |
dc.identifier.isi | WOS:000225550300033 | - |
dc.publisher.place | United States | en_HK |
dc.identifier.scopusauthorid | Yang, D=7404800756 | en_HK |
dc.identifier.scopusauthorid | Gao, Q=7202743913 | en_HK |
dc.identifier.scopusauthorid | Zheng, BF=7201781469 | en_HK |
dc.identifier.scopusauthorid | Zhu, NY=7201449530 | en_HK |
dc.identifier.issnl | 0022-3263 | - |