Files in this item
Quinidine-Catalysed Enantioselective Synthesis of 6- and 4-Trifluoromethyl-Substituted Dihydropyrans
Item metadata
dc.contributor.author | Kasten, Kevin | |
dc.contributor.author | Cordes, David Bradford | |
dc.contributor.author | Slawin, Alexandra Martha Zoya | |
dc.contributor.author | Smith, Andrew David | |
dc.date.accessioned | 2017-06-23T23:33:59Z | |
dc.date.available | 2017-06-23T23:33:59Z | |
dc.date.issued | 2016-07 | |
dc.identifier | 242924163 | |
dc.identifier | 82f38897-83cd-49dd-bd72-68af4d44beb4 | |
dc.identifier | 84976871784 | |
dc.identifier | 000380138700023 | |
dc.identifier.citation | Kasten , 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.201600583 | en |
dc.identifier.issn | 1434-193X | |
dc.identifier.other | ORCID: /0000-0002-2104-7313/work/36567489 | |
dc.identifier.other | ORCID: /0000-0002-5366-9168/work/28023976 | |
dc.identifier.other | ORCID: /0000-0002-9527-6418/work/56861607 | |
dc.identifier.uri | https://hdl.handle.net/10023/11074 | |
dc.description | The 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.abstract | The 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.extent | 1644864 | |
dc.language.iso | eng | |
dc.relation.ispartof | European Journal of Organic Chemistry | en |
dc.subject | Organocatalysis | en |
dc.subject | Enantioselective catalysis | en |
dc.subject | Oxygen heterocycles | en |
dc.subject | QD Chemistry | en |
dc.subject | NDAS | en |
dc.subject.lcc | QD | en |
dc.title | Quinidine-Catalysed Enantioselective Synthesis of 6- and 4-Trifluoromethyl-Substituted Dihydropyrans | en |
dc.type | Journal article | en |
dc.contributor.sponsor | European Commission | en |
dc.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.contributor.institution | University of St Andrews. Biomedical Sciences Research Complex | en |
dc.contributor.institution | University of St Andrews. EaSTCHEM | en |
dc.identifier.doi | https://doi.org/10.1002/ejoc.201600583 | |
dc.description.status | Peer reviewed | en |
dc.date.embargoedUntil | 2017-06-23 | |
dc.identifier.url | http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201600583/full#footer-support-info | en |
dc.identifier.grantnumber | N/A | en |
This item appears in the following Collection(s)
Items in the St Andrews Research Repository are protected by copyright, with all rights reserved, unless otherwise indicated.