Biocatalytic Approach to Chiral -Nitroalcohols by Enantioselective Alcohol Dehydrogenase-Mediated Reduction of -Nitroketones

that is based on the enzyme-mediated reduction of ?-nitroketones has been scarcelyconsidered. In this work, the use of commercial alcohol dehydrogenases (ADHs) for the reductionof aromatic and aliphatic nitroketones is investigated. High conversions and enantioselectivities canbe achieved with two specific ADHs, affording either the (S) or (R)-enantiomer of the correspondingnitroalcohols. The reaction conditions are carefully tuned to preserve the stability of the reducedproduct, and to avoid the hydrolytic degradation of the starting substrate. The further manipulation of the enantioenriched nitroalcohols into Boc-protected amminoalcohols is also described