Canadian Journal of Chemistry p. 2950 - 2956 (1982)
Update date:2022-09-26
Topics:
Jones, J. Bryan
Takemura, Tetsuo
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.
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