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Enantioselective stereodivergent nucleophile-dependent isothiourea-catalysed domino reactions

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dc.contributor.authorMatviitsuk, Anastassia
dc.contributor.authorTaylor, James Edward
dc.contributor.authorCordes, David Bradford
dc.contributor.authorSlawin, Alexandra Martha Zoya
dc.contributor.authorSmith, Andrew David
dc.date.accessioned2016-10-12T09:30:09Z
dc.date.available2016-10-12T09:30:09Z
dc.date.issued2016-12-05
dc.identifier245237155
dc.identifier7cab6d38-0ff6-4470-8799-cda59ad142da
dc.identifier000388471700032
dc.identifier84991080752
dc.identifier000388471700032
dc.identifier.citationMatviitsuk , A , Taylor , J E , Cordes , D B , Slawin , A M Z & Smith , A D 2016 , ' Enantioselective stereodivergent nucleophile-dependent isothiourea-catalysed domino reactions ' , Chemistry - A European Journal , vol. 22 , no. 49 , pp. 17748-17757 . https://doi.org/10.1002/chem.201603318en
dc.identifier.issn0947-6539
dc.identifier.otherORCID: /0000-0002-2104-7313/work/36567482
dc.identifier.otherORCID: /0000-0002-5366-9168/work/28023968
dc.identifier.otherORCID: /0000-0002-9527-6418/work/56861553
dc.identifier.urihttps://hdl.handle.net/10023/9649
dc.descriptionWe thank the European Research Council under the European Union’s Seventh Framework Programme (FP7/2007–2013) ERC grant agreement no. 279850 (J.E.T.) and the EPSRC (EP/J018139/1, A.M.). ADS thanks the Royal Society for a Wolfson Research Merit Award.en
dc.description.abstractα,β-Unsaturated acyl ammoniums generated from the reaction of α,β-unsaturated 2,4,6-trichlorophenol (TCP) esters bearing a pendent enone with an isothiourea organocatalyst are versatile intermediates in a range of enantioselective nucleophile-dependent domino processes to form complex products of diverse topology with excellent stereoselectivity. Use of either 1,3-dicarbonyls, acyl benzothiazoles, or acyl benzimidazoles as nucleophiles allows three distinct, diastereodivergent domino reaction pathways to be accessed to form various fused polycyclic cores containing multiple contiguous stereocentres.
dc.format.extent10
dc.format.extent1267163
dc.language.isoeng
dc.relation.ispartofChemistry - A European Journalen
dc.subjectDomino reactionsen
dc.subjectEnantioselective synthesisen
dc.subjectLewis baseen
dc.subjectOrganocatalysisen
dc.subjectα,β-unsaturated acyl ammoniumen
dc.subjectQD Chemistryen
dc.subjectA General Worksen
dc.subjectDASen
dc.subject.lccQDen
dc.subject.lccAen
dc.titleEnantioselective stereodivergent nucleophile-dependent isothiourea-catalysed domino reactionsen
dc.typeJournal articleen
dc.contributor.sponsorEPSRCen
dc.contributor.sponsorThe Royal Societyen
dc.contributor.sponsorEPSRCen
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.doi10.1002/chem.201603318
dc.description.statusPeer revieweden
dc.identifier.grantnumberEP/J018139/1en
dc.identifier.grantnumberWM140071en
dc.identifier.grantnumberEP/J018139/1en


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