The stereochemistry of the addition of titanium enolates of N-propionyl-oxazolidin-2-ones to 5- and 6-membered N-acyliminium ions

dc.creatorPilli, RA
dc.creatorAlves, CD
dc.creatorBockelmann, MA
dc.creatorMascarenhas, YP
dc.creatorNery, JG
dc.creatorVencato, I
dc.date1999
dc.dateAPR 9
dc.date2014-12-02T16:27:20Z
dc.date2015-11-26T17:56:35Z
dc.date2014-12-02T16:27:20Z
dc.date2015-11-26T17:56:35Z
dc.date.accessioned2018-03-29T00:40:13Z
dc.date.available2018-03-29T00:40:13Z
dc.identifierTetrahedron Letters. Pergamon-elsevier Science Ltd, v. 40, n. 15, n. 2891, n. 2894, 1999.
dc.identifier0040-4039
dc.identifierWOS:000079465500008
dc.identifier10.1016/S0040-4039(99)00398-6
dc.identifierhttp://www.repositorio.unicamp.br/jspui/handle/REPOSIP/72501
dc.identifierhttp://www.repositorio.unicamp.br/handle/REPOSIP/72501
dc.identifierhttp://repositorio.unicamp.br/jspui/handle/REPOSIP/72501
dc.identifier.urihttp://repositorioslatinoamericanos.uchile.cl/handle/2250/1291286
dc.descriptionThe stereochemistry of the addition of the N-propionyl titanium enolates 2a and 2b to 5- and 6-membered 2-ethoxycarbamates 1a-f was investigated. The addition proceeded stereoselectively to afford the corresponding (2S,1'S)-2-substituted pyrrolidines as the major diastereoisomer. Despite the lack of reactivity between 2-ethoxypiperidine 1b and N-propionyl titanium enolates 2a and 2b, less bulky carbamate groups on 2-ethoxypiperidines 1d and 1f restored reactivity and the corresponding 2-substituted piperidines were obtained in moderate to good yields although with poor diastereoselection (C) 1999 Elsevier Science Ltd. All rights reserved.
dc.description40
dc.description15
dc.description2891
dc.description2894
dc.languageen
dc.publisherPergamon-elsevier Science Ltd
dc.publisherOxford
dc.publisherInglaterra
dc.relationTetrahedron Letters
dc.relationTetrahedron Lett.
dc.rightsfechado
dc.rightshttp://www.elsevier.com/about/open-access/open-access-policies/article-posting-policy
dc.sourceWeb of Science
dc.subjecttitanium enolates
dc.subjectN-acyliminium ion
dc.subject2-substituted pyrrolidines and piperidine
dc.subjectbeta-amino acid derivatives
dc.subjectBeta-amino Acids
dc.titleThe stereochemistry of the addition of titanium enolates of N-propionyl-oxazolidin-2-ones to 5- and 6-membered N-acyliminium ions
dc.typeArtículos de revistas


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