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- Title
Isothiourea-Catalysed Acylative Kinetic Resolution of Aryl-Alkenyl (sp<sup>2</sup> vs. sp<sup>2</sup>) Substituted Secondary Alcohols.
- Authors
Musolino, Stefania F.; Ojo, O. Stephen; Westwood, Nicholas J.; Taylor, James E.; Smith, Andrew D.
- 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.
- Subjects
ENZYME analysis; ANHYDRIDE analysis; ENANTIOMERS analysis; ARYL group; ALKENYL group
- Publication
Chemistry - A European Journal, 2016, Vol 22, Issue 52, p18916
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201604788