Dynamic Kinetic Resolution of Racemic β-Haloalcohols: Direct Access to Enantioenriched Epoxides
Journal of the American Chemical Society2008Vol. 130(41), pp. 13508–13509
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Robert M. Haak, Florian Berthiol, Thomas Jerphagnon, Arnaud Gayet, Chiara Tarabiono, Christiaan P. Postema, Vincent Ritleng, Michel Pfeffer, Dick B. Janssen, Adriaan J. Minnaard, Ben L. Feringa, Johannes G. de Vries
Abstract
The direct chemo-enzymatic DKR of racemic beta-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 beta-haloalcohols.
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