Isothiourea‐Catalysed Acylative Kinetic Resolution of Aryl–Alkenyl (sp² vs. sp²) Substituted Secondary Alcohols

Abstract

Abstract The non‐enzymatic acylative kinetic resolution of challenging aryl–alkenyl (sp 2 vs. sp 2 ) 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 (sp 2 vs. sp 2 ) substituted secondary alcohol is demonstrated, giving access to >1 g of each of the product enantiomers both in 99:1 e.r .