Practical two-step synthesis of an enantiopure aliphatic terminal (S)-epoxide based on reduction of haloalkanones with ``Designer Cells''

Berkessel A, Rollmann C, Chamouleau F, Labs S, May O, Gröger H (2007)
ADVANCED SYNTHESIS & CATALYSIS 349(17-18): 2697-2704.

Journal Article | Published | English

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Abstract
A practical biocatalytic method for the synthesis of aliphatic P-halogenated (S)-alcohols as epoxide precursors by means of an enantioselective reduction of the corresponding ketones with recombinant whole cells, bearing an alcohol dehydrogenase and a glucose dehydrogenase, was developed. The biotransformations operate at high substrate concentrations of up to 208 g/L, and afford the (S)-beta-halohydrins with both high conversions of > 95 % and enantioselectivities of > 99 % ee. Base-induced cyclization of the P-halohydrin intermediates gave the desired (S)-epoxides in high yield and enantiomeric purity (> 99 % ee).
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Berkessel A, Rollmann C, Chamouleau F, Labs S, May O, Gröger H. Practical two-step synthesis of an enantiopure aliphatic terminal (S)-epoxide based on reduction of haloalkanones with ``Designer Cells''. ADVANCED SYNTHESIS & CATALYSIS. 2007;349(17-18):2697-2704.
Berkessel, A., Rollmann, C., Chamouleau, F., Labs, S., May, O., & Gröger, H. (2007). Practical two-step synthesis of an enantiopure aliphatic terminal (S)-epoxide based on reduction of haloalkanones with ``Designer Cells''. ADVANCED SYNTHESIS & CATALYSIS, 349(17-18), 2697-2704.
Berkessel, A., Rollmann, C., Chamouleau, F., Labs, S., May, O., and Gröger, H. (2007). Practical two-step synthesis of an enantiopure aliphatic terminal (S)-epoxide based on reduction of haloalkanones with ``Designer Cells''. ADVANCED SYNTHESIS & CATALYSIS 349, 2697-2704.
Berkessel, A., et al., 2007. Practical two-step synthesis of an enantiopure aliphatic terminal (S)-epoxide based on reduction of haloalkanones with ``Designer Cells''. ADVANCED SYNTHESIS & CATALYSIS, 349(17-18), p 2697-2704.
A. Berkessel, et al., “Practical two-step synthesis of an enantiopure aliphatic terminal (S)-epoxide based on reduction of haloalkanones with ``Designer Cells''”, ADVANCED SYNTHESIS & CATALYSIS, vol. 349, 2007, pp. 2697-2704.
Berkessel, A., Rollmann, C., Chamouleau, F., Labs, S., May, O., Gröger, H.: Practical two-step synthesis of an enantiopure aliphatic terminal (S)-epoxide based on reduction of haloalkanones with ``Designer Cells''. ADVANCED SYNTHESIS & CATALYSIS. 349, 2697-2704 (2007).
Berkessel, Albrecht, Rollmann, Claudia, Chamouleau, Francoise, Labs, Stefanie, May, Oliver, and Gröger, Harald. “Practical two-step synthesis of an enantiopure aliphatic terminal (S)-epoxide based on reduction of haloalkanones with ``Designer Cells''”. ADVANCED SYNTHESIS & CATALYSIS 349.17-18 (2007): 2697-2704.
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