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Regio‐ and Stereoselective Reduction of Diketones and Oxidation of Diols by Biocatalytic Hydrogen Transfer
Author(s) -
Edegger Klaus,
Stampfer Wolfgang,
Seisser Birgit,
Faber Kurt,
Mayer Sandra F.,
Oehrlein Reinhold,
Hafner Andreas,
Kroutil Wolfgang
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200500839
Subject(s) - chemistry , stereoselectivity , ketone , steric effects , alcohol , hydrogen , organic chemistry , alcohol oxidation , stereochemistry , catalysis
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)