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Isothiourea-catalysed acylative kinetic resolution of aryl-alkenyl (sp2 vs. sp2) substituted secondary alcohols

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dc.contributor.authorMusolino, Stefania F.
dc.contributor.authorOjo, O. Stephen
dc.contributor.authorWestwood, Nicholas J.
dc.contributor.authorTaylor, James E.
dc.contributor.authorSmith, Andrew D.
dc.date.accessioned2016-12-02T00:33:40Z
dc.date.available2016-12-02T00:33:40Z
dc.date.issued2016-12-23
dc.identifier.citationMusolino , S F , Ojo , O S , Westwood , N J , Taylor , J E & Smith , A D 2016 , ' Isothiourea-catalysed acylative kinetic resolution of aryl-alkenyl (sp 2 vs. sp 2 ) substituted secondary alcohols ' , Chemistry - A European Journal , vol. 22 , no. 52 , pp. 18916-18922 . https://doi.org/10.1002/chem.201604788en
dc.identifier.issn0947-6539
dc.identifier.otherPURE: 246879570
dc.identifier.otherPURE UUID: 4562cef9-6ac1-4f08-a715-30c19e07454a
dc.identifier.otherScopus: 85006791371
dc.identifier.otherORCID: /0000-0002-2104-7313/work/36567481
dc.identifier.otherORCID: /0000-0003-0630-0138/work/56424140
dc.identifier.otherWOS: 000393219300039
dc.identifier.urihttps://hdl.handle.net/10023/9922
dc.descriptionWe would like to thank the Engineering and Physical Sciences Research Council and CRITICAT Centre for Doctoral Training [Ph.D. studentship to S.F.M.; Grant code: EP/L016419/1 and EP/J018139/1] and The Leverhulme Trust [Early Career Fellowship to J.E.T.; ECF-2014-005] for financial support. A.D.S. thanks the Royal Society for a Wolfson Merit Award.en
dc.description.abstractThe non-enzymatic acylative kinetic resolution of challenging aryl–alkenyl (sp2 vs. sp2) substituted secondary alcohols is described, with effective enantiodiscrimination achieved using the isothiourea organocatalyst HyperBTM (1 mol %) and isobutyric anhydride. The kinetic resolution of a wide range of aryl–alkenyl substituted alcohols has been evaluated, with either electron-rich or naphthyl aryl substituents in combination with an unsubstituted vinyl substituent providing the highest selectivity (S=2–1980). The use of this protocol for the gram-scale (2.5 g) kinetic resolution of a model aryl–vinyl (sp2 vs. sp2) substituted secondary alcohol is demonstrated, giving access to >1 g of each of the product enantiomers both in 99:1 e.r.
dc.format.extent8
dc.language.isoeng
dc.relation.ispartofChemistry - A European Journalen
dc.rights© 2016 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.subjectKinetic resolutionen
dc.subjectAcylationen
dc.subjectOrganocatalysisen
dc.subjectIsothioureaen
dc.subjectRenewable resourcesen
dc.subjectQD Chemistryen
dc.subjectTP Chemical technologyen
dc.subjectDASen
dc.subjectSDG 7 - Affordable and Clean Energyen
dc.subject.lccQDen
dc.subject.lccTPen
dc.titleIsothiourea-catalysed acylative kinetic resolution of aryl-alkenyl (sp2 vs. sp2) substituted secondary alcoholsen
dc.typeJournal articleen
dc.contributor.sponsorEPSRCen
dc.contributor.sponsorEPSRCen
dc.contributor.sponsorThe Leverhulme Trusten
dc.contributor.sponsorEPSRCen
dc.description.versionPublisher PDFen
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.doihttps://doi.org/10.1002/chem.201604788
dc.description.statusPeer revieweden
dc.identifier.grantnumberEP/L016419/1en
dc.identifier.grantnumberEP/J018139/1en
dc.identifier.grantnumberECF-2014-005en
dc.identifier.grantnumberEP/J018139/1en


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