Show simple item record

Files in this item

Thumbnail

Item metadata

dc.contributor.authorRichmond, Edward
dc.contributor.authorLing, Kenneth Bruce
dc.contributor.authorDuguet, Nicolas Fabien Denis
dc.contributor.authorManton, Lois B.
dc.contributor.authorÇelebi-Ölçüm, Nihan
dc.contributor.authorLam, Yu-hong
dc.contributor.authorAlsancak, Sezen
dc.contributor.authorSlawin, Alexandra Martha Zoya
dc.contributor.authorHouk, K. N.
dc.contributor.authorSmith, Andrew David
dc.date.accessioned2015-12-03T00:11:28Z
dc.date.available2015-12-03T00:11:28Z
dc.date.issued2015-02-14
dc.identifier.citationRichmond , E , Ling , K B , Duguet , N F D , Manton , L B , Çelebi-Ölçüm , N , Lam , Y , Alsancak , S , Slawin , A M Z , Houk , K N & Smith , A D 2015 , ' An asymmetric pericyclic cascade approach to 3-alkyl-3-aryloxindoles : generality, applications and mechanistic investigations ' , Organic & Biomolecular Chemistry , vol. 13 , no. 6 , pp. 1807-1817 . https://doi.org/10.1039/c4ob02526aen
dc.identifier.issn1477-0520
dc.identifier.otherPURE: 159434783
dc.identifier.otherPURE UUID: 84837478-b71a-4cd2-ae3c-34376f9884d2
dc.identifier.otherScopus: 84921994301
dc.identifier.otherWOS: 000349032400026
dc.identifier.otherPubMed: 25501712
dc.identifier.otherORCID: /0000-0002-2104-7313/work/36567502
dc.identifier.otherORCID: /0000-0002-9527-6418/work/56861322
dc.identifier.urihttp://hdl.handle.net/10023/7881
dc.descriptionThe authors thank the Royal Society for a URF (ADS), Cancer Research UK (ER), the Leverhulme Trust (ND) and EPSRC (KBL) for funding. We are also grateful to the National Science Foundation (USA) for financial support of the research at UCLA (KNH).en
dc.description.abstractThe reaction of L-serine derived N-arylnitrones with alkylarylketenes generates asymmetric 3-alkyl-3-aryloxindoles in good to excellent yields (up to 93%) and excellent enantioselectivity (up to 98% ee) via a pericyclic cascade process. The optimization, scope and applications of this transformation are reported, alongside further synthetic and computational investigations. The preparation of the enantiomer of a Roche anti-cancer agent (RO4999200) 1 (96% ee) in three steps demonstrates the potential utility of this methodology.
dc.format.extent11
dc.language.isoeng
dc.relation.ispartofOrganic & Biomolecular Chemistryen
dc.rights© The Royal Society of Chemistry 2014. This work is made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at http://pubs.rsc.org/en/Content/ArticleLanding/2015/OB/C4OB02526A#!divAbstracten
dc.subjectAmino acidsen
dc.subjectAnti-cancer agentsen
dc.subjectCascade processen
dc.subjectComputational investigationen
dc.subjectL-serineen
dc.subjectPotential utilityen
dc.subjectQD Chemistryen
dc.subjectDASen
dc.subject.lccQDen
dc.titleAn asymmetric pericyclic cascade approach to 3-alkyl-3-aryloxindoles : generality, applications and mechanistic investigationsen
dc.typeJournal articleen
dc.description.versionPostprinten
dc.contributor.institutionUniversity of St Andrews.School of Chemistryen
dc.contributor.institutionUniversity of St Andrews.Biomedical Sciences Research Complexen
dc.contributor.institutionUniversity of St Andrews.EaSTCHEMen
dc.identifier.doihttps://doi.org/10.1039/c4ob02526a
dc.description.statusPeer revieweden
dc.date.embargoedUntil2015-12-03


This item appears in the following Collection(s)

Show simple item record