Show simple item record

Files in this item


Item metadata

dc.contributor.authorYoung, Claire M.
dc.contributor.authorTaylor, James E.
dc.contributor.authorSmith, Andrew D.
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 .
dc.identifier.otherPURE: 258563119
dc.identifier.otherPURE UUID: e85c986f-599c-4da7-b2c9-222cac72c267
dc.identifier.otherORCID: /0000-0002-2104-7313/work/56424214
dc.identifier.otherScopus: 85065861147
dc.identifier.otherWOS: 000468000000009
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:
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.relation.ispartofOrganic & Biomolecular Chemistryen
dc.rightsCopyright © 2019 The Author(s). This work has been 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
dc.subjectQD Chemistryen
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.description.statusPeer revieweden

This item appears in the following Collection(s)

Show simple item record