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 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.

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(S)-2-DecanolC10H22OEe = 92%[α]D20=+9.8 (c 1.00, EtOH)Source of chirality: deracemisation, asymmetric synthesisAbsolute configuration: (S)