Steric effects in the hypervalent iodine oxidation of ketones |
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| Authors: | Robert M. Moriarty Indra Prakash H.A. Musallam |
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| Affiliation: | Department of Chemistry University of Illinois at Chicago Chicago, Illinois 60680, U.S.A.;Department of the Army Walter Reed Army Institute of Research Walter Reed Army Medical Center Washington, D.C. 20307, U.S.A. |
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| Abstract: | Oxidation of 3-cholestanone (1) with C6H5I(OAc)2 or o-OIC6H4COOH or C6H5IO2 in KOH/MeOH yields 2 α-carbomethoxy-A-norcholestane (2). This result is interpreted on mechanistic grounds and compared with the course of the reaction with other sterically hindered ketones such as friedelin, 3-keto, 12-keto, 17-keto steroids, and 2,2,6,6-tetramethyl-4-piperidone. |
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