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dc.contributor.authorYoung, Claire M.
dc.contributor.authorTaylor, James E.
dc.contributor.authorSmith, Andrew D.
dc.date.accessioned2020-04-10T23:32:10Z
dc.date.available2020-04-10T23:32:10Z
dc.date.issued2019-05-21
dc.identifier258563119
dc.identifiere85c986f-599c-4da7-b2c9-222cac72c267
dc.identifier85065861147
dc.identifier000468000000009
dc.identifier.citationYoung , C M , Taylor , J E & Smith , A D 2019 , ' Evaluating aryl esters as bench-stable C(1)-ammonium enolate precursors in catalytic, enantioselective Michael addition-lactonisations ' , Organic & Biomolecular Chemistry , vol. 17 , no. 19 , pp. 4747-4752 . https://doi.org/10.1039/C9OB00703Ben
dc.identifier.issn1477-0520
dc.identifier.otherORCID: /0000-0002-2104-7313/work/56424214
dc.identifier.urihttps://hdl.handle.net/10023/19781
dc.descriptionWe thank the European Research Council under the European Union’s Seventh Framework Programme (FP7/2007-2013) ERC Grant Agreement no. 279850 (CMY, JET). ADS thanks the Royal Society for a Wolfson Merit Award. We also thank the EPSRC UK National Mass Spectrometry Facility at Swansea University. The data underpinning this research can be found at DOI: https://doi.org/10.17630/cb133261-b58e-4d72-b380-c877c993dc5den
dc.description.abstractAn evaluation of a range of aryl, alkyl and vinyl esters as prospective C(1)-ammonium enolate precursors in enantioselective Michael addition-lactonisation processes with (E)-trifluoromethylenones using isothiourea catalysis is reported. Electron deficient aryl esters are required for reactivity, with 2,4,6-trichlorophenyl esters providing optimal product yields. Catalyst screening showed that tetramisole was the most effective isothiourea catalyst, giving the desired dihydropyranone product in excellent yield and stereoselectivity (up to 90:10 dr and 98:2 er). The scope and limitations of this process have been evaluated, with a range of diester products being generated after ring-opening with MeOH to give stereodefined dihydropyranones with excellent stereocontrol (10 examples, typically ~90:10 dr and >95:5 er).
dc.format.extent481339
dc.language.isoeng
dc.relation.ispartofOrganic & Biomolecular Chemistryen
dc.subjectQD Chemistryen
dc.subjectDASen
dc.subject.lccQDen
dc.titleEvaluating aryl esters as bench-stable C(1)-ammonium enolate precursors in catalytic, enantioselective Michael addition-lactonisationsen
dc.typeJournal articleen
dc.contributor.sponsorEuropean Commissionen
dc.contributor.sponsorThe Royal Societyen
dc.contributor.institutionUniversity of St Andrews. School of Chemistryen
dc.contributor.institutionUniversity of St Andrews. EaSTCHEMen
dc.contributor.institutionUniversity of St Andrews. Biomedical Sciences Research Complexen
dc.identifier.doi10.1039/C9OB00703B
dc.description.statusPeer revieweden
dc.date.embargoedUntil2020-04-11
dc.identifier.grantnumberN/Aen
dc.identifier.grantnumberWM140071en


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