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Article: Further studies on sultones derived from carbene cyclization cycloaddition cascades

TitleFurther studies on sultones derived from carbene cyclization cycloaddition cascades
Authors
Issue Date2015
PublisherElsevier. The Journal's web site is located at http://www.elsevier.com/locate/tet
Citation
Tetrahedron, 2015, v. 71, p. 5925-5931 How to Cite?
AbstractA sulfonyl-stabilized diazoketone underwent an efficient rhodium-catalyzed cascade reaction with an internal vinylsulfonate unit to give a tricyclic sultone as a single diastereomer. Nucleophilic addition of a vinyl Grignard reagent to the ketone of the resultant arylsulfonyl-substituted cycloadduct was stereocomplementary with respect to vinyl Grignard addition to corresponding ester-substituted substrates. The latter tricyclic compounds were chemoselectively transformed into vinylsultones via β-elimination in good yield.
Persistent Identifierhttp://hdl.handle.net/10722/231685

 

DC FieldValueLanguage
dc.contributor.authorGross, T-
dc.contributor.authorHerrmann, T-
dc.contributor.authorShi, B-
dc.contributor.authorJager, A-
dc.contributor.authorChiu, P-
dc.contributor.authorMetz, P-
dc.date.accessioned2016-09-20T05:24:51Z-
dc.date.available2016-09-20T05:24:51Z-
dc.date.issued2015-
dc.identifier.citationTetrahedron, 2015, v. 71, p. 5925-5931-
dc.identifier.urihttp://hdl.handle.net/10722/231685-
dc.description.abstractA sulfonyl-stabilized diazoketone underwent an efficient rhodium-catalyzed cascade reaction with an internal vinylsulfonate unit to give a tricyclic sultone as a single diastereomer. Nucleophilic addition of a vinyl Grignard reagent to the ketone of the resultant arylsulfonyl-substituted cycloadduct was stereocomplementary with respect to vinyl Grignard addition to corresponding ester-substituted substrates. The latter tricyclic compounds were chemoselectively transformed into vinylsultones via β-elimination in good yield.-
dc.languageeng-
dc.publisherElsevier. The Journal's web site is located at http://www.elsevier.com/locate/tet-
dc.relation.ispartofTetrahedron-
dc.rightsPosting accepted manuscript (postprint): © <year>. This manuscript version is made available under the CC-BY-NC-ND 4.0 license http://creativecommons.org/licenses/by-nc-nd/4.0/-
dc.titleFurther studies on sultones derived from carbene cyclization cycloaddition cascades-
dc.typeArticle-
dc.identifier.emailChiu, P: pchiu@hku.hk-
dc.identifier.authorityChiu, P=rp00680-
dc.identifier.doi10.1016/j.tet.2015.05.095-
dc.identifier.hkuros265997-
dc.identifier.volume71-
dc.identifier.spage5925-
dc.identifier.epage5931-

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