Silylation-Based Kinetic Resolution of Monofunctional Secondary Alcohols

The nucleophilic small molecule catalyst (−)-tetramisole was found to catalyze the kinetic resolution of monofunctional secondary alcohols via enantioselective silylation. Optimization of this new methodology allows for selectivity factors up to 25 utilizing commercially available reagents and mild...

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Bibliographic Details
Published in:Organic letters 2011-08, Vol.13 (15), p.3794-3797
Main Authors: Sheppard, Cody I, Taylor, Jessica L, Wiskur, Sheryl L
Format: Article
Language:English
Subjects:
Alcohols - chemistry
Catalysis
Kinetics
Molecular Structure
Stereoisomerism
Tetramisole - chemistry
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Summary:The nucleophilic small molecule catalyst (−)-tetramisole was found to catalyze the kinetic resolution of monofunctional secondary alcohols via enantioselective silylation. Optimization of this new methodology allows for selectivity factors up to 25 utilizing commercially available reagents and mild reaction conditions.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol2012617