Stereochemical aspects of the vanadium-catalysed epoxidation of conformationally biased cyclohex-2-en-1-ols by alkyl hydroperoxides

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Abstract
In the vanadium-catalysed epoxidation of cis- and trans-5-t-butylcyclohex-2-enol the trans-(pseudoaxial) alcohol is epoxidised ca. 34 times faster than the cis-isomer. A significant competing process is oxidation to αβ-unsaturated ketone, and this becomes the predominant reaction in the case of the cis-alcohol.