Isothiourea-catalysed acylative kinetic resolution of aryl-alkenyl (sp2 vs. sp2) substituted secondary alcohols
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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.
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
Chemistry - A European Journal
© 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.
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.
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