Dynamic Kinetic Resolution of Racemic β-Haloalcohols: Direct Access to Enantioenriched Epoxides

The direct chemo-enzymatic DKR of racemic β-haloalcohols is reported, yielding the corresponding optically active epoxides in a single step. The mutant haloalcohol dehalogenase HheC Cys153Ser Trp249Phe is used for the asymmetric ring closure, whereas racemization of the remaining enantiomer of the h...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2008-10, Vol.130 (41), p.13508-13509
Main Authors: Haak, Robert M, Berthiol, Florian, Jerphagnon, Thomas, Gayet, Arnaud J. A, Tarabiono, Chiara, Postema, Christiaan P, Ritleng, Vincent, Pfeffer, Michel, Janssen, Dick B, Minnaard, Adriaan J, Feringa, Ben L, de Vries, Johannes G
Format: Article
Language:English
Subjects:
Alcohols - chemistry
Catalysis
Chemical Sciences
Cyclization
Epoxy Compounds - chemistry
Halogens - chemistry
Kinetics
Molecular Structure
Stereoisomerism
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Summary:The direct chemo-enzymatic DKR of racemic β-haloalcohols is reported, yielding the corresponding optically active epoxides in a single step. The mutant haloalcohol dehalogenase HheC Cys153Ser Trp249Phe is used for the asymmetric ring closure, whereas racemization of the remaining enantiomer of the haloalcohol is achieved using the new iridacycle 3, one of the most effective racemization catalysts to date for β-haloalcohols.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja805128x