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Article: Et2AlCl-promoted asymmetric phenylseleno group transfer radical cyclization reactions of unsaturated β-hydroxy esters

TitleEt2AlCl-promoted asymmetric phenylseleno group transfer radical cyclization reactions of unsaturated β-hydroxy esters
Authors
Issue Date2004
PublisherAmerican 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?
AbstractWe 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 Identifierhttp://hdl.handle.net/10722/167876
ISSN
2015 Impact Factor: 4.785
2015 SCImago Journal Rankings: 2.095
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorYang, Den_HK
dc.contributor.authorGao, Qen_HK
dc.contributor.authorZheng, BFen_HK
dc.contributor.authorZhu, NYen_HK
dc.date.accessioned2012-10-08T03:12:24Z-
dc.date.available2012-10-08T03:12:24Z-
dc.date.issued2004en_HK
dc.identifier.citationJournal Of Organic Chemistry, 2004, v. 69 n. 25, p. 8821-8828en_HK
dc.identifier.issn0022-3263en_HK
dc.identifier.urihttp://hdl.handle.net/10722/167876-
dc.description.abstractWe 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.languageengen_US
dc.publisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/jocen_HK
dc.relation.ispartofJournal of Organic Chemistryen_HK
dc.subject.meshAluminum Compounds - Chemistryen_US
dc.subject.meshCyclizationen_US
dc.subject.meshEsters - Chemical Synthesisen_US
dc.subject.meshFree Radicals - Chemistryen_US
dc.subject.meshHydroxy Acids - Chemical Synthesisen_US
dc.subject.meshMolecular Conformationen_US
dc.subject.meshOrganometallic Compounds - Chemistryen_US
dc.subject.meshSelenium - Chemistryen_US
dc.titleEt2AlCl-promoted asymmetric phenylseleno group transfer radical cyclization reactions of unsaturated β-hydroxy estersen_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.doi10.1021/jo048322zen_HK
dc.identifier.pmid15575763-
dc.identifier.scopuseid_2-s2.0-10044246186en_HK
dc.identifier.hkuros98425-
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-10044246186&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume69en_HK
dc.identifier.issue25en_HK
dc.identifier.spage8821en_HK
dc.identifier.epage8828en_HK
dc.identifier.isiWOS:000225550300033-
dc.publisher.placeUnited Statesen_HK
dc.identifier.scopusauthoridYang, D=7404800756en_HK
dc.identifier.scopusauthoridGao, Q=7202743913en_HK
dc.identifier.scopusauthoridZheng, BF=7201781469en_HK
dc.identifier.scopusauthoridZhu, NY=7201449530en_HK

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