Optical Rotatory Dispersion Studies. 136. Enzymatic Reduction of 2-Methyl-2-(trideuteriomethyl)cyclohexane-1,3-dione. Unusual Conformation of 2,2-Dimethyl-3-hydroxycyclohexanone

Article abstract of DOI:10.1021/jo00172a021

The enzymatic reduction of 2-methyl-2-(trideuteriomethyl)cyclohexane-1,3-dione with Kloeckera magna is not stereospecific with respect to the α center.The reaction product, 2-methyl-2-(trideuteriomethyl)-3-hydroxycyclohexanone, was shown to possess the 3S configuration.The circular dichroism and X-ray crystallographic data lead to the unexpected conclusion that the reduction product assumes the conformation with an axially oriented hydroxyl group.