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Isothiourea-catalysed acylative kinetic resolution of aryl-alkenyl (sp2 vs. sp2) substituted secondary alcohols
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dc.contributor.author | Musolino, Stefania F. | |
dc.contributor.author | Ojo, O. Stephen | |
dc.contributor.author | Westwood, Nicholas J. | |
dc.contributor.author | Taylor, James E. | |
dc.contributor.author | Smith, Andrew D. | |
dc.date.accessioned | 2016-12-02T00:33:40Z | |
dc.date.available | 2016-12-02T00:33:40Z | |
dc.date.issued | 2016-12-23 | |
dc.identifier | 246879570 | |
dc.identifier | 4562cef9-6ac1-4f08-a715-30c19e07454a | |
dc.identifier | 85006791371 | |
dc.identifier | 000393219300039 | |
dc.identifier.citation | Musolino , 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.201604788 | en |
dc.identifier.issn | 0947-6539 | |
dc.identifier.other | ORCID: /0000-0002-2104-7313/work/36567481 | |
dc.identifier.other | ORCID: /0000-0003-0630-0138/work/56424140 | |
dc.identifier.uri | https://hdl.handle.net/10023/9922 | |
dc.description | We 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.abstract | The 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.extent | 8 | |
dc.format.extent | 915314 | |
dc.language.iso | eng | |
dc.relation.ispartof | Chemistry - A European Journal | en |
dc.subject | Kinetic resolution | en |
dc.subject | Acylation | en |
dc.subject | Organocatalysis | en |
dc.subject | Isothiourea | en |
dc.subject | Renewable resources | en |
dc.subject | QD Chemistry | en |
dc.subject | TP Chemical technology | en |
dc.subject | DAS | en |
dc.subject | SDG 7 - Affordable and Clean Energy | en |
dc.subject.lcc | QD | en |
dc.subject.lcc | TP | en |
dc.title | Isothiourea-catalysed acylative kinetic resolution of aryl-alkenyl (sp2 vs. sp2) substituted secondary alcohols | en |
dc.type | Journal article | en |
dc.contributor.sponsor | EPSRC | en |
dc.contributor.sponsor | EPSRC | en |
dc.contributor.sponsor | The Leverhulme Trust | en |
dc.contributor.sponsor | EPSRC | en |
dc.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.contributor.institution | University of St Andrews. EaSTCHEM | en |
dc.contributor.institution | University of St Andrews. Biomedical Sciences Research Complex | en |
dc.identifier.doi | https://doi.org/10.1002/chem.201604788 | |
dc.description.status | Peer reviewed | en |
dc.identifier.grantnumber | EP/L016419/1 | en |
dc.identifier.grantnumber | EP/J018139/1 | en |
dc.identifier.grantnumber | ECF-2014-005 | en |
dc.identifier.grantnumber | EP/J018139/1 | en |
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