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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.identifier242924163
dc.identifier82f38897-83cd-49dd-bd72-68af4d44beb4
dc.identifier84976871784
dc.identifier000380138700023
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.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.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.format.extent1644864
dc.language.isoeng
dc.relation.ispartofEuropean Journal of Organic Chemistryen
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.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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