A biocatalytic one-pot oxidation/reduction sequence for the deracemisation of a sec-alcohol

Biocatalytic deracemisation via inversion of rac-2-decanol was accomplished by a combined oxidation/reduction sequence using the same ‘single’ catalyst for both steps. Overall, the ( R)-alcohol was inverted to the corresponding ( S)-alcohol. Lyophilised cells of various Rhodococci spp. were tested f...

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Bibliographic Details
Published in:Tetrahedron: asymmetry 2007-02, Vol.18 (2), p.276-281
Main Authors: Voss, Constance V., Gruber, Christian C., Kroutil, Wolfgang
Format: Article
Language:English
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Summary:Biocatalytic deracemisation via inversion of rac-2-decanol was accomplished by a combined oxidation/reduction sequence using the same ‘single’ catalyst for both steps. Overall, the ( R)-alcohol was inverted to the corresponding ( S)-alcohol. Lyophilised cells of various Rhodococci spp. were tested for the unselective oxidation of the racemic sec-alcohol using acetone as the hydrogen acceptor in the first step. For the second step, the stereoselective asymmetric reduction of the corresponding ketone, 2-propanol was employed as the hydrogen donor. Employing lyophilised cells of Rhodococcus sp. CBS 717.73 racemic 2-decanol was transformed to ( S)-2-decanol with excellent enantiomeric excess (92% ee) and yield (82% isolated yield) in the combined one-pot oxidation/reduction sequence.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2007.01.013