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dc.contributor.authorYoung, Claire M.
dc.contributor.authorStark, Daniel G.
dc.contributor.authorWest, Thomas H.
dc.contributor.authorTaylor, James E.
dc.contributor.authorSmith, Andrew D.
dc.date.accessioned2017-10-20T23:32:15Z
dc.date.available2017-10-20T23:32:15Z
dc.date.issued2016-11-07
dc.identifier.citationYoung , C M , Stark , D G , West , T H , Taylor , J E & Smith , A D 2016 , ' Exploiting the imidazolium effect in base-free ammonium enolate generation : synthetic and mechanistic studies ' , Angewandte Chemie International Edition , vol. 55 , no. 46 , pp. 14394-14399 . https://doi.org/10.1002/anie.201608046en
dc.identifier.issn1433-7851
dc.identifier.otherPURE: 246307143
dc.identifier.otherPURE UUID: d43c41f8-0524-4751-8a15-16fb08b73639
dc.identifier.otherScopus: 84992504728
dc.identifier.otherORCID: /0000-0002-2104-7313/work/36567485
dc.identifier.otherWOS: 000387028000035
dc.identifier.urihttp://hdl.handle.net/10023/11898
dc.descriptionThe authors thank the European Research Council under the European Union’s Seventh Framework Programme (FP7/2007-2013) ERC Grant Agreement no. 279850 (CMY, THW, JET). ADS thanks the Royal Society for a Wolfson Merit Award.en
dc.description.abstractN-Acyl imidazoles and catalytic isothiourea hydrochloride salts function as ammonium enolate precursors in the absence of base. Enantioselective Michael addition-cyclization reactions using different α,β-unsaturated Michael acceptors have been performed to form dihydropyranones and dihydropyridinones with high stereoselectivity. Detailed mechanistic studies using RPKA have revealed the importance of the “imidazolium” effect in ammonium enolate formation and have highlighted key differences with traditional base-mediated processes.
dc.format.extent6
dc.language.isoeng
dc.relation.ispartofAngewandte Chemie International Editionen
dc.rightsCopyright © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. 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 https://doi.org/10.1002/anie.201608046en
dc.subjectImidazolium effecten
dc.subjectIsothiourea catalysisen
dc.subjectMechanistic studyen
dc.subjectMichael additionen
dc.subjectN-acyl imidazolesen
dc.subjectQD Chemistryen
dc.subjectDASen
dc.subjectBDCen
dc.subjectR2Cen
dc.subject.lccQDen
dc.titleExploiting the imidazolium effect in base-free ammonium enolate generation : synthetic and mechanistic studiesen
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/10.1002/anie.201608046
dc.description.statusPeer revieweden
dc.date.embargoedUntil2017-10-20


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