The deprotonation and alkylation of 1-methylcyclohexa-2,5-diene-1-carboxylic acid has been investigated under a range of conditions. In all cases, the formation of compounds 14 was found to be completely stereoselective, although compound 14c was formed as an impurity when alkyl iodides were used as electrophiles, and doubly-alkylated compounds 17 were formed in some cases when alkyl bromides were used.

Diastereoselective alkylation reactions of 1-methylcyclohexa-2,5-diene-1-carboxylic acid produce compounds 14 with minimal impurities, making them useful for synthesis of pharmaceuticals and nutraceuticals.

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Diastereoselective alkylation reactions of 1-methylcyclohexa-2,5-diene-1-carboxylic acid.

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