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Article: Diastereoselective atom transfer radical cyclization reactions of unsaturated α-bromo oxazolidinone imides catalyzed by Lewis acids

TitleDiastereoselective atom transfer radical cyclization reactions of unsaturated α-bromo oxazolidinone imides catalyzed by Lewis acids
Authors
Issue Date2003
PublisherPergamon. The Journal's web site is located at http://www.elsevier.com/locate/tetasy
Citation
Tetrahedron Asymmetry, 2003, v. 14 n. 19, p. 2927-2937 How to Cite?
AbstractA new Lewis acid-catalyzed atom transfer radical cyclization reaction of unsaturated α-bromo oxazolidinone imides is reported. In the presence of Lewis acids such as Mg(ClO4)2 and Yb(OTf)3, a series of trans cyclic products was obtained in high yield (up to 87%) between 0°C and room temperature. The loading of strong Lewis acids, such as Yb(OTf)3, can be reduced to 0.1 equiv. without significantly compromising the yield. Excellent diastereoselectivity could be achieved by using 1,2-stereocontrol or a chiral oxazolidinone auxiliary. For substrates 1e and 1f bearing a β-methyl substituent and the chiral auxiliary, (S)-(-)-4-benzyl-5,5-dimethyl-2-oxazolidinone, respectively, the diastereomeric ratio of the products was greater than 50:1. © 2003 Elsevier Ltd. All rights reserved.
Persistent Identifierhttp://hdl.handle.net/10722/167918
ISSN
2015 Impact Factor: 2.108
2015 SCImago Journal Rankings: 0.806
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorYang, Den_HK
dc.contributor.authorZheng, BFen_HK
dc.contributor.authorGu, Sen_HK
dc.contributor.authorChan, PWHen_HK
dc.contributor.authorZhu, NYen_HK
dc.date.accessioned2012-10-08T03:12:54Z-
dc.date.available2012-10-08T03:12:54Z-
dc.date.issued2003en_HK
dc.identifier.citationTetrahedron Asymmetry, 2003, v. 14 n. 19, p. 2927-2937en_HK
dc.identifier.issn0957-4166en_HK
dc.identifier.urihttp://hdl.handle.net/10722/167918-
dc.description.abstractA new Lewis acid-catalyzed atom transfer radical cyclization reaction of unsaturated α-bromo oxazolidinone imides is reported. In the presence of Lewis acids such as Mg(ClO4)2 and Yb(OTf)3, a series of trans cyclic products was obtained in high yield (up to 87%) between 0°C and room temperature. The loading of strong Lewis acids, such as Yb(OTf)3, can be reduced to 0.1 equiv. without significantly compromising the yield. Excellent diastereoselectivity could be achieved by using 1,2-stereocontrol or a chiral oxazolidinone auxiliary. For substrates 1e and 1f bearing a β-methyl substituent and the chiral auxiliary, (S)-(-)-4-benzyl-5,5-dimethyl-2-oxazolidinone, respectively, the diastereomeric ratio of the products was greater than 50:1. © 2003 Elsevier Ltd. All rights reserved.en_HK
dc.languageengen_US
dc.publisherPergamon. The Journal's web site is located at http://www.elsevier.com/locate/tetasyen_HK
dc.relation.ispartofTetrahedron Asymmetryen_HK
dc.titleDiastereoselective atom transfer radical cyclization reactions of unsaturated α-bromo oxazolidinone imides catalyzed by Lewis acidsen_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.doi10.1016/j.tetasy.2003.06.001en_HK
dc.identifier.scopuseid_2-s2.0-1842473730en_HK
dc.identifier.hkuros91171-
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-1842473730&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume14en_HK
dc.identifier.issue19en_HK
dc.identifier.spage2927en_HK
dc.identifier.epage2937en_HK
dc.identifier.isiWOS:000185941200015-
dc.publisher.placeUnited Kingdomen_HK
dc.identifier.scopusauthoridYang, D=7404800756en_HK
dc.identifier.scopusauthoridZheng, BF=7201781469en_HK
dc.identifier.scopusauthoridGu, S=36901908100en_HK
dc.identifier.scopusauthoridChan, PWH=13607033800en_HK
dc.identifier.scopusauthoridZhu, NY=7201449530en_HK

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