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Quinidine-Catalysed Enantioselective Synthesis of 6- and 4-Trifluoromethyl-Substituted Dihydropyrans

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dc.contributor.authorKasten, Kevin
dc.contributor.authorCordes, David Bradford
dc.contributor.authorSlawin, Alexandra Martha Zoya
dc.contributor.authorSmith, Andrew David
dc.date.accessioned2017-06-23T23:33:59Z
dc.date.available2017-06-23T23:33:59Z
dc.date.issued2016-07
dc.identifier.citationKasten , K , Cordes , D B , Slawin , A M Z & Smith , A D 2016 , ' Quinidine-Catalysed Enantioselective Synthesis of 6- and 4-Trifluoromethyl-Substituted Dihydropyrans ' , European Journal of Organic Chemistry , vol. 2016 , no. 21 . https://doi.org/10.1002/ejoc.201600583en
dc.identifier.issn1434-193X
dc.identifier.otherPURE: 242924163
dc.identifier.otherPURE UUID: 82f38897-83cd-49dd-bd72-68af4d44beb4
dc.identifier.otherScopus: 84976871784
dc.identifier.otherORCID: /0000-0002-2104-7313/work/36567489
dc.identifier.otherORCID: /0000-0002-5366-9168/work/28023976
dc.identifier.otherORCID: /0000-0002-9527-6418/work/56861607
dc.identifier.otherWOS: 000380138700023
dc.identifier.urihttps://hdl.handle.net/10023/11074
dc.descriptionThe authors thank the Royal Society for a University Research Fellowship (ADS) and the European Research Council under the European Union’s Seventh Framework Programme (FP7/2007-2013), ERC Grant Agreement No. 279850 (KK), the authors also thank the EPSRC UK National Mass Spectrometry Facility at Swansea University.en
dc.description.abstractThe cinchona alkaloid-catalysed enantioselective formal [4+2] cycloaddition of ethyl 2,3-butadienoate with a range of 1,1,1-trifluoro- and 4,4,4-trifluorobutenones is investigated for the preparation of stereodefined 6- and 4-trifluoromethyl-substituted dihydropyrans. Quinidine proved to be the optimal catalyst, generating the desired products in up to 98 % ee and 81 % yield. Stereo- and chemoselective derivatization of the dihydropyrans through hydrogenation is explored.
dc.language.isoeng
dc.relation.ispartofEuropean Journal of Organic Chemistryen
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://dx.doi.org/10.1002/ejoc.201600583en
dc.subjectOrganocatalysisen
dc.subjectEnantioselective catalysisen
dc.subjectOxygen heterocyclesen
dc.subjectQD Chemistryen
dc.subjectNDASen
dc.subject.lccQDen
dc.titleQuinidine-Catalysed Enantioselective Synthesis of 6- and 4-Trifluoromethyl-Substituted Dihydropyransen
dc.typeJournal articleen
dc.contributor.sponsorEuropean Commissionen
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/ejoc.201600583
dc.description.statusPeer revieweden
dc.date.embargoedUntil2017-06-23
dc.identifier.urlhttp://onlinelibrary.wiley.com/doi/10.1002/ejoc.201600583/full#footer-support-infoen
dc.identifier.grantnumberN/Aen


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