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Exploring the scope of the isothiourea-mediated synthesis of dihydropyridinones

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dc.contributor.authorYeh, Pei-Pei
dc.contributor.authorDaniels, David Sydney Bernard
dc.contributor.authorFallan, Charlene
dc.contributor.authorGould, Eoin Rory
dc.contributor.authorSimal Fernandez, Carmen
dc.contributor.authorTaylor, James Edward
dc.contributor.authorSlawin, Alexandra Martha Zoya
dc.contributor.authorSmith, Andrew David
dc.date.accessioned2015-12-02T00:11:25Z
dc.date.available2015-12-02T00:11:25Z
dc.date.issued2015-02-21
dc.identifier159431608
dc.identifier3d62bcc8-046d-4a92-9156-44eb131911a3
dc.identifier84922675627
dc.identifier000349401300034
dc.identifier25553730
dc.identifier.citationYeh , P-P , Daniels , D S B , Fallan , C , Gould , E R , Simal Fernandez , C , Taylor , J E , Slawin , A M Z & Smith , A D 2015 , ' Exploring the scope of the isothiourea-mediated synthesis of dihydropyridinones ' , Organic & Biomolecular Chemistry , vol. 13 , no. 7 , pp. 2177-2191 . https://doi.org/10.1039/c4ob02408gen
dc.identifier.issn1477-0520
dc.identifier.otherORCID: /0000-0002-2104-7313/work/36567501
dc.identifier.otherORCID: /0000-0002-8987-5561/work/27750840
dc.identifier.otherORCID: /0000-0002-9527-6418/work/56861429
dc.identifier.urihttps://hdl.handle.net/10023/7877
dc.descriptionThe authors thank the Royal Society for a University Research Fellowship (ADS), the EU (IEF for CS) and the European Research Council under the European Union’s Seventh Framework Programme (FP7/2007-2013) ERC Grant Agreement No. 279850 (JET and CF) and the EPSRC grant numbers EP/J018139/1 (DSBD) and EP/K00445X/1 (EG) for funding.en
dc.description.abstractThe exploration and expansion of the scope of the isothiourea-mediated synthesis of dihydropyridinones is presented. The use of ketimines derived from α,β-unsaturated γ-ketoesters as the Michael acceptor in a Michael addition / lactamisation cascade gives access to a range of dihydropyridinones with high enantioselectivity. The nature of the N-sulfonyl group present on the ketimine is extensively investigated, with further studies into derivatisation of the dihydropyridinone core also reported.
dc.format.extent529970
dc.language.isoeng
dc.relation.ispartofOrganic & Biomolecular Chemistryen
dc.subjectDerivatisationen
dc.subjectHigh enantioselectivityen
dc.subjectIsothioureaen
dc.subjectKetiminesen
dc.subjectKeto esteren
dc.subjectMichael acceptorsen
dc.subjectMichael additionsen
dc.subjectSulfonyl groupsen
dc.subjectQD Chemistryen
dc.subjectDASen
dc.subject.lccQDen
dc.titleExploring the scope of the isothiourea-mediated synthesis of dihydropyridinonesen
dc.typeJournal articleen
dc.contributor.sponsorEPSRCen
dc.contributor.sponsorEPSRCen
dc.contributor.sponsorEPSRCen
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/c4ob02408g
dc.description.statusPeer revieweden
dc.date.embargoedUntil2015-12-02
dc.identifier.grantnumberEP/J018139/1en
dc.identifier.grantnumberEP/J018139/1en
dc.identifier.grantnumberEP/K039210/1en
dc.identifier.grantnumberN/Aen


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