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dc.contributor.authorHallett, D.J.
dc.contributor.authorGerhard, U.
dc.contributor.authorGoodacre, S.C.
dc.contributor.authorHitzel, L.
dc.contributor.authorSparey, T.J.
dc.contributor.authorThomas, S.
dc.contributor.authorRowley, M.
dc.contributor.authorBall, R.G.
dc.date.accessioned2012-08-23T14:00:57Z
dc.date.available2012-08-23T14:00:57Z
dc.date.issued2000-08-11
dc.identifier.citationHallett , D J , Gerhard , U , Goodacre , S C , Hitzel , L , Sparey , T J , Thomas , S , Rowley , M & Ball , R G 2000 , ' Neighboring group participation of the indole nucleus : An unusual DAST-mediated rearrangerment reaction ' , Journal of Organic Chemistry , vol. 65 , no. 16 , pp. 4984-4993 . https://doi.org/10.1021/jo0004759
dc.identifier.issn0022-3263
dc.identifier.otherPURE: 940562
dc.identifier.otherPURE UUID: 8691d4fa-8459-478f-8ed2-aeee42701685
dc.identifier.otherScopus: 0034637620
dc.identifier.urihttp://hdl.handle.net/2299/8948
dc.descriptionCopyright 2004 Elsevier Science B.V., Amsterdam. All rights reserved.
dc.description.abstractA rearrangement reaction involving the indole nucleus was investigated using stereochemical markers and low-temperature NMR experiments. Treatment of(3S,4S)-3-hydroxy-4-(2-phenyl-1H-indol-3-yl)-piperidine-1-carboxylic acid benzyl ester (> 90% ee) with diethylaminosulfur trifluoride gave stereospecifically (3S,4S)-4-fluoro-3-(2-phenyl-1H-indol-3-yl)-piperidine-1-carboxylic acid benzyl ester (> 90% ee) with complete regioselectivity. The initial formation of a reactive spirocyclopropyl-3H-indole intermediate is believed to be responsible for the stereo- and regiochemical outcome of the reaction.en
dc.format.extent10
dc.language.isoeng
dc.relation.ispartofJournal of Organic Chemistry
dc.titleNeighboring group participation of the indole nucleus : An unusual DAST-mediated rearrangerment reactionen
dc.contributor.institutionDepartment of Pharmacy
dc.contributor.institutionHealth & Human Sciences Research Institute
dc.description.statusPeer reviewed
dc.identifier.urlhttp://www.scopus.com/inward/record.url?scp=0034637620&partnerID=8YFLogxK
dcterms.dateAccepted2000-08-11
rioxxterms.versionofrecordhttps://doi.org/10.1021/jo0004759
rioxxterms.typeJournal Article/Review
herts.preservation.rarelyaccessedtrue


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