Regio- and Stereoselective Reduction of Diketones and Oxidation of Diols by Biocatalytic Hydrogen Transfer

Autor: Edegger, Klaus, Stampfer, Wolfgang, Seisser, Birgit, Faber, Kurt, Mayer, Sandra F., Oehrlein, Reinhold, Hafner, Andreas, Kroutil, Wolfgang
Zdroj: European Journal of Organic Chemistry; April 2006, Vol. 2006 Issue: 8 p1904-1909, 6p
Abstrakt: The asymmetric reduction of symmetrical and nonsymmetrical diketones as well as the stereoselective oxidation of various diols by biocatalytic hydrogen transfer was investigated by employing lyophilized cells of Rhodococcus ruber DSM 44541 containing alcohol dehydrogense ADH-‘A’. Symmetrical and nonsymmetrical diketones at the (ω-1)- and (ω-2)-positions are reduced to the Prelog product with high stereopreference, while sterically more demanding ketone moieties, for example those at the (ω-3)-position, remain unchanged. For the oxidation mode, differentiation between primary and secondary alcohols is achieved, and the (S)-configured secondary alcohols at the (ω-1)- and (ω-2)-positions are oxidized preferentially. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
Databáze: Supplemental Index