Isothiourea‐Catalysed Acylative Kinetic Resolution of Aryl–Alkenyl (sp2 vs. sp2) Substituted Secondary Alcohols |
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Authors: | Stefania F Musolino Dr O Stephen Ojo Prof Nicholas J Westwood Dr James E Taylor Prof Andrew D Smith |
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Institution: | EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, St Andrews, UK |
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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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Keywords: | acylation isothiourea kinetic resolution organocatalysis renewable resources |
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