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Published on: October 30, 2018
Isothiourea-Catalysed Acylative Kinetic Resolution of Aryl-Alkenyl (sp2 vs. sp2 ) Substituted Secondary Alcohols
Stefania F Musolino1, O Stephen Ojo1, Nicholas J Westwood1
1EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, St Andrews, KY16 9ST, UK.
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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