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dc.contributor.authorZhang, Shuyue
dc.contributor.authorBacheley, Lucas
dc.contributor.authorYoung, Claire Mary
dc.contributor.authorStark, Daniel Graham
dc.contributor.authorO'Riordan, Timothy
dc.contributor.authorSlawin, Alexandra Martha Zoya
dc.contributor.authorSmith, Andrew David
dc.date.accessioned2020-10-09T14:30:01Z
dc.date.available2020-10-09T14:30:01Z
dc.date.issued2020-10
dc.identifier.citationZhang , S , Bacheley , L , Young , C M , Stark , D G , O'Riordan , T , Slawin , A M Z & Smith , A D 2020 , ' Isothiourea-catalyzed functionalization of pyrrolyl- and indolylacetic acid : enantioselective synthesis of dihydropyridinones and one-pot synthesis of pyridinones ' , Asian Journal of Organic Chemistry , vol. 9 , no. 10 , pp. 1562-1566 . https://doi.org/10.1002/ajoc.202000290en
dc.identifier.issn2193-5815
dc.identifier.otherPURE: 268542463
dc.identifier.otherPURE UUID: a113b3cf-7b58-4778-9a72-cfe240fcf546
dc.identifier.otherORCID: /0000-0002-2104-7313/work/77131143
dc.identifier.otherORCID: /0000-0002-9527-6418/work/77131207
dc.identifier.otherWOS: 000546624300001
dc.identifier.otherScopus: 85087709766
dc.identifier.urihttp://hdl.handle.net/10023/20754
dc.descriptionFunding: ERC under the European Union's Seventh Framework Programme (FP7/2007–2013) / ERC grant agreement no 279850. We thank Syngenta and EPSRC grant No. EP/K503162/1 (DGS), ADS thanks the Royal Society for a Wolfson Research Merit Award.en
dc.description.abstractA protocol for the isothiourea‐catalyzed enantioselective functionalization of pyrrolyl‐ and indolylacetic acids has been developed. Stereodefined dihydropyridinones are accessed through formal [4+2] cycloaddition of an in situ generated isothiouronium enolate with α,β‐unsaturated ketimines. The dihydropyridinones are obtained in moderate to excellent yield (26–97%), excellent diastereocontrol (all >95 : 5 dr) and moderate to excellent enantiocontrol (75 : 25–99 : 1 er). An unusual elimination of pyrrole or indole from the dihydropyridinone to access achiral pyridinones was observed and could be selectively promoted. A further one‐pot synthesis using an acyl imidazole was developed to give pyridinones in good to excellent yields (67–91%).
dc.format.extent5
dc.language.isoeng
dc.relation.ispartofAsian Journal of Organic Chemistryen
dc.rightsCopyright © 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.en
dc.subjectHeterocycle synthesisen
dc.subjectOrganocatalysisen
dc.subjectPyrrole eliminationen
dc.subjectIndole eliminationen
dc.subjectIsothioureaen
dc.subjectQD Chemistryen
dc.subjectDASen
dc.subject.lccQDen
dc.titleIsothiourea-catalyzed functionalization of pyrrolyl- and indolylacetic acid : enantioselective synthesis of dihydropyridinones and one-pot synthesis of pyridinonesen
dc.typeJournal articleen
dc.description.versionPublisher PDFen
dc.contributor.institutionUniversity of St Andrews.EaSTCHEMen
dc.contributor.institutionUniversity of St Andrews.School of Chemistryen
dc.identifier.doihttps://doi.org/10.1002/ajoc.202000290
dc.description.statusPeer revieweden


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