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Enantioselective isothiourea-catalysed trans-dihydropyridinone synthesis using saccharin-derived ketimines : scope and limitations

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dc.contributor.authorStark, Daniel Graham
dc.contributor.authorYoung, Claire Mary
dc.contributor.authorO'Riordan, Timothy J C
dc.contributor.authorSlawin, Alexandra Martha Zoya
dc.contributor.authorSmith, Andrew David
dc.date.accessioned2016-08-19T09:40:10Z
dc.date.available2016-08-19T09:40:10Z
dc.date.issued2016-09-14
dc.identifier244566038
dc.identifieraa8bd179-6ffe-44f5-a791-a64dc27659d9
dc.identifier84984656800
dc.identifier000382058000012
dc.identifier.citationStark , D G , Young , C M , O'Riordan , T J C , Slawin , A M Z & Smith , A D 2016 , ' Enantioselective isothiourea-catalysed trans -dihydropyridinone synthesis using saccharin-derived ketimines : scope and limitations ' , Organic & Biomolecular Chemistry , vol. 14 , no. 34 , pp. 8068-8073 . https://doi.org/10.1039/C6OB01473Aen
dc.identifier.issn1477-0520
dc.identifier.otherORCID: /0000-0002-2104-7313/work/36567487
dc.identifier.otherORCID: /0000-0002-9527-6418/work/56861938
dc.identifier.urihttps://hdl.handle.net/10023/9332
dc.descriptionThe authors thank Syngenta and the EPSRC (grant code EP/K503162/1) (DGS) for funding. The European Research Council under the European Union’s Seventh Framework Programme (FP7/2007-2013) ERC Grant Agreement No. 279850 is also acknowledged (CMY). ADS thanks the Royal Society for a Wolfson Research Merit Award. We also thank the EPSRC UK National Mass Spectrometry Facility at Swansea University.en
dc.description.abstractThe catalytic enantioselective synthesis of a range of trans-dihydropyridinones from aryl-, heteroaryl- and alkenylacetic acids and saccharin-derived ketimines with good to excellent stereocontrol (15 examples, up to >95:5 dr, up to >99:1 er) is reported. After extensive optimisation, HyperBTM proved the optimal isothiourea catalyst for this transformation at −78 °C, giving trans-dihydropyridones with generally excellent levels of diastereo- and enantioselectivity.
dc.format.extent6
dc.format.extent2152979
dc.language.isoeng
dc.relation.ispartofOrganic & Biomolecular Chemistryen
dc.subjectQD Chemistryen
dc.subjectDASen
dc.subject.lccQDen
dc.titleEnantioselective isothiourea-catalysed trans-dihydropyridinone synthesis using saccharin-derived ketimines : scope and limitationsen
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.doi10.1039/C6OB01473A
dc.description.statusPeer revieweden
dc.identifier.urlhttp://www.rsc.org/suppdata/c6/ob/c6ob01473a/c6ob01473a1.pdfen
dc.identifier.grantnumberN/Aen


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