cistrans Selectivity of Enzyme-Catalyzed Additions to 4-Substituted Cyclohexanones—Correlation with the Prelog/Ringold Model of Enzymatic Hydrogenation


  • Enzyme-catalyzed reactions, Part 44. This work was supported by Degussa AG. We thank Dr. B. Miehlich for modeling calculations and Dr. A. Baro for assistance in preparing the manuscript. Part 43: F. Effenberger, S. Oßwald, Tetrahedron: Asymmetry2001, 12, 2581–2587.


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The choice of enzyme is decisive: for the enzyme-catalyzed addition of HCN to 4-substituted cyclohexanones 1, highly selective biocatalysts are available that allow control to yield the cis or the trans addition product 2. Modeling of the S enzyme–substrate complex reveals remarkable parallels with the Prelog/Ringold model of the LADH-catalyzed hydrogenation of cyclohexanones.