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.
Original language | English |
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Pages (from-to) | 18916-18922 |
Number of pages | 7 |
Journal | Chemistry - A European Journal |
Volume | 22 |
Issue number | 52 |
Early online date | 30 Nov 2016 |
DOIs | |
Publication status | Published - 21 Dec 2016 |
Keywords
- acylation
- isothiourea
- kinetic resolution
- organocatalysis
- renewable resources
ASJC Scopus subject areas
- General Chemistry