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dc.contributor.authorShu, Chang
dc.contributor.authorLiu, Honglei
dc.contributor.authorSlawin, Alexandra
dc.contributor.authorCarpenter-Warren, Cameron L.
dc.contributor.authorSmith, Andrew David
dc.date.accessioned2019-11-15T13:30:04Z
dc.date.available2019-11-15T13:30:04Z
dc.date.issued2019-10-23
dc.identifier.citationShu , C , Liu , H , Slawin , A , Carpenter-Warren , C L & Smith , A D 2019 , ' Isothiourea-catalysed enantioselective Michael addition of N-heterocyclic pronucleophiles to α,β-unsaturated aryl esters ' , Chemical Science , vol. Advance Article . https://doi.org/10.1039/C9SC04303Aen
dc.identifier.issn2041-6520
dc.identifier.otherPURE: 261991297
dc.identifier.otherPURE UUID: 0e9bb6e1-1faa-4c61-b609-ed9384766ee0
dc.identifier.otherORCID: /0000-0002-2104-7313/work/63716535
dc.identifier.otherORCID: /0000-0002-9527-6418/work/63716633
dc.identifier.otherScopus: 85076988829
dc.identifier.otherWOS: 000503486800024
dc.identifier.urihttps://hdl.handle.net/10023/18937
dc.descriptionThe research leading to these results (C. S., H. L.) has received funding from the Royal Society Newton Fellowship Programme. A.D.S. thanks the Royal Society for a Wolfson Research Merit Award.en
dc.description.abstractThe isothiourea-catalysed enantioselective Michael addition of 3-aryloxindole and 4-substituted-dihydropyrazol-3-one pronucleophiles to α,β-unsaturated p-nitrophenyl esters is reported. This process generates products containing two contiguous stereocentres, one quaternary, in good yields and excellent enantioselectivities (>30 examples, up to > 95 : 5 dr and 99 : 1 er). This protocol harnesses the multifunctional ability of p-nitrophenoxide to promote effective catalysis. In contrast to previous methodologies using tertiary amine Lewis bases, in which the pronucleophile was used as the solvent, this work allows bespoke pronucleophiles to be used in stoichiometric quantities.
dc.format.extent7
dc.language.isoeng
dc.relation.ispartofChemical Scienceen
dc.rightsCopyright © 2019 The Author(s). Open Access Article. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.en
dc.subjectQD Chemistryen
dc.subjectDASen
dc.subject.lccQDen
dc.titleIsothiourea-catalysed enantioselective Michael addition of N-heterocyclic pronucleophiles to α,β-unsaturated aryl estersen
dc.typeJournal articleen
dc.contributor.sponsorThe Royal Societyen
dc.contributor.sponsorThe Royal Societyen
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/10.1039/C9SC04303A
dc.description.statusPeer revieweden
dc.identifier.grantnumberNF170330en
dc.identifier.grantnumberWM140071en


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