A study of factors controlling the combined C-H activation/Cope rearrangement
Ovalles, Stephanie R.
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An optimization study was conducted on the reaction between arylvinyl diazoacetates and 1,4-cyclohexadiene in the presence of rhodium carboxylate catalysts. The goal of this study was to determine whether the product distribution of the reaction could be controlled to yield only the desired combined C-H activation/cope rearrangement product. The effect of solvent on chemoselectivity was found to be minor. The enantiomeric excess remained virtually the same for the solvents that were examined for the desired product. The structure of the chiral catalysts had a relatively large impact on the product distribution. Dirhodium prolinates were superior to other catalysts with respect to both selectivity for the combined C-H activation/Cope rearrangement and also enantiomeric excess of the products. The most dominating effect seems to be the structure of the carbenoid and catalyst structure.