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Article: Ligand Effect and Control of E- and Z-Selectivity in the Silver-Catalyzed Synthesis of 4-Bromooxazolines

TitleLigand Effect and Control of E- and Z-Selectivity in the Silver-Catalyzed Synthesis of 4-Bromooxazolines
Authors
Keywordsligand effects
silver
hydroamination
heterocycles
Issue Date2015
Citation
Advanced Synthesis and Catalysis, 2015, v. 357, n. 11, p. 2485-2491 How to Cite?
Abstract© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. The stereospecific intramolecular hydroamination of alkynyl trichloroacetimidates catalyzed by bis(pyridyl)silver(I) complexes to form 1,3-oxazolines and oxazines has been investigated in greater detail. The rate of the reaction is profoundly influenced by the electronic character of the pyridyl ligand; leading to optimized conditions whereby reactions can be completed at ambient temperature with catalyst loadings as low as 1 mol%, while maintaining stereoselectivity towards the (Z)-isomer. Further investigations into establishing the role of the ligand, and the synthesis of (E)-isomer, are also presented.
Persistent Identifierhttp://hdl.handle.net/10722/219805
ISSN
2015 Impact Factor: 6.453
2015 SCImago Journal Rankings: 2.729

 

DC FieldValueLanguage
dc.contributor.authorWong, Valerie H L-
dc.contributor.authorWhite, Andrew J P-
dc.contributor.authorHor, T. S Andy-
dc.contributor.authorHii, King Kuok-
dc.date.accessioned2015-09-23T02:58:00Z-
dc.date.available2015-09-23T02:58:00Z-
dc.date.issued2015-
dc.identifier.citationAdvanced Synthesis and Catalysis, 2015, v. 357, n. 11, p. 2485-2491-
dc.identifier.issn1615-4150-
dc.identifier.urihttp://hdl.handle.net/10722/219805-
dc.description.abstract© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. The stereospecific intramolecular hydroamination of alkynyl trichloroacetimidates catalyzed by bis(pyridyl)silver(I) complexes to form 1,3-oxazolines and oxazines has been investigated in greater detail. The rate of the reaction is profoundly influenced by the electronic character of the pyridyl ligand; leading to optimized conditions whereby reactions can be completed at ambient temperature with catalyst loadings as low as 1 mol%, while maintaining stereoselectivity towards the (Z)-isomer. Further investigations into establishing the role of the ligand, and the synthesis of (E)-isomer, are also presented.-
dc.languageeng-
dc.relation.ispartofAdvanced Synthesis and Catalysis-
dc.subjectligand effects-
dc.subjectsilver-
dc.subjecthydroamination-
dc.subjectheterocycles-
dc.titleLigand Effect and Control of E- and Z-Selectivity in the Silver-Catalyzed Synthesis of 4-Bromooxazolines-
dc.typeArticle-
dc.description.natureLink_to_subscribed_fulltext-
dc.identifier.doi10.1002/adsc.201500157-
dc.identifier.scopuseid_2-s2.0-84938956407-
dc.identifier.volume357-
dc.identifier.issue11-
dc.identifier.spage2485-
dc.identifier.epage2491-
dc.identifier.eissn1615-4169-

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