title: Isothiourea-Catalysed Acylative Kinetic Resolution of Aryl-Alkenyl (sp2vs. sp2) Substituted Secondary Alcohols.
abstract: The non-enzymatic acylative kinetic resolution of challenging aryl-alkenyl (sp2vs. 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 (sp2vs. sp2) substituted secondary alcohol is demonstrated, giving access to >1 g of each of the product enantiomers both in 99:1 e.r.
authors: EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, St Andrews, KY16 9ST, UK.
authors: Stefania F
authors: SF
authors: Musolino
authors: EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, St Andrews, KY16 9ST, UK.
authors: O Stephen
authors: OS
authors: Ojo
authors: EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, St Andrews, KY16 9ST, UK.
authors: Nicholas J
authors: NJ
authors: Westwood
authors: EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, St Andrews, KY16 9ST, UK.
authors: James E
authors: JE
authors: Taylor
authors: EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, St Andrews, KY16 9ST, UK.
authors: Andrew D
authors: AD
authors: Smith
keywords: acylation; isothiourea; kinetic resolution; organocatalysis; renewable resources