Optical rotatory dispersion studies. 136. Enzymic reduction of 2-methyl-2-(trideuteriomethyl) cyclohexane-1, 3-dione. Unusual conformation of 2, 2-dimethyl-3- …

…, G Barth, K Kieslich, PD Strong, WL Duax…

Index: Lu, Yucheng; Barth, Guenther; Kieslich, Klaus; Strong, Phyllis D.; Duax, William L.; Djerassi, Carl Journal of Organic Chemistry, 1983 , vol. 48, # 24 p. 4549 - 4554

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Citation Number: 29

Abstract

The enzymatic reduction of 2-methyl-2-(trideuteriomethyl) cyclohexane-1, 3-dione with Kloeckera magna is not stereospecific with respect to the a 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 ...