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

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Author(s)

Stefania F. Musolino, O. Stephen Ojo, Nicholas J. Westwood, James E. Taylor, Andrew D. Smith

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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.
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Original languageEnglish
Pages (from-to)18916-18922
Number of pages8
JournalChemistry - A European Journal
Volume22
Issue number52
Early online date30 Nov 2016
DOIs
StatePublished - 23 Dec 2016

    Research areas

  • Kinetic resolution, Acylation, Organocatalysis, Isothiourea, Renewable resources

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