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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.
Highlights
Non-enzymatic, acylative kinetic resolution (KR) is a powerful method for the preparation of enantiomerically enriched alcohols.[1]
In terms of substrate scope, non-enzymatic acylative KRs are most commonly trialed on benzylic secondary alcohols for which the catalytic acylating agent must differentiate between the enantiomers of alcohols bearing a planar aryl and a tetrahedral alkyl substituent in order to obtain high selectivity (Figure 1 a)
Highly selective methods have been developed for the KR of both alkynyl–alkyl and alkenyl–alkyl substituted secondary alcohols
Summary
Non-enzymatic, acylative kinetic resolution (KR) is a powerful method for the preparation of enantiomerically enriched alcohols.[1]. In terms of substrate scope, non-enzymatic acylative KRs are most commonly trialed on benzylic secondary alcohols for which the catalytic acylating agent must differentiate between the enantiomers of alcohols bearing a planar aryl (sp2) and a tetrahedral alkyl (sp3) substituent in order to obtain high selectivity (Figure 1 a). Highly selective methods have been developed for the KR of both alkynyl–alkyl (sp vs sp3) and alkenyl–alkyl (sp vs sp3) substituted secondary alcohols. In these systems the acylating agent must differentiate between the enantiomers of alcohols with a planar p-system and a tetrahedral sp hybridized substituent. A number of Lewis base organocatalysts have been utilized for the acylative KR of alkenyl–alkyl (sp vs. sp3) allylic alcohols (Figure 1 b).[2,3,4,5,6,7] Fu used planar-chiral DMAP-derived ferrocene catalyst 1 and acetic anhydride for the KR of a range of allylic
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