Enzymes in organic synthesis. 28. Reinvestigation of the horse liver alcohol dehydrogenase-catalyzed reductions of 2-alkylcyclohexanones. Identification of cis-alkylcyclohexanols as minor products.

Article abstract of DOI:10.1139/v82-423

The formation of cis-2-alkylcyclohexanol products from horse liver alcohol dehydrogenase-catalyzed reductions of 2-alkylcyclohexanones has been detected for the first time.The cis-alcohols are minor (<4percent) products, with the isomeric trans-products being heavily predominant under all conditions. cis-Alcohol production can be suppressed by suitable manipulation of the reaction conditions.Exclusive formation of the trans-alcohols is favoured by operating in an appropriate buffer such as Tris-HCl at the lowest / and pH conditions possible, and by minimizing the reaction time.The results parallel the cis-alcohol formation observed previously with the analogous 3-alkyltetrahydropyran-4-one substrates.