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. 2012 May 21;10(19):3859-65.
doi: 10.1039/c2ob25211b. Epub 2012 Apr 4.

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

Nicholas J Bennett  1 , Mark C Elliott, Natalie L Hewitt, Benson M Kariuki, Clare A Morton, Steven A Raw, Simone Tomasi
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Diastereoselective alkylation reactions of 1-methylcyclohexa-2,5-diene-1-carboxylic acid

Nicholas J Bennett et al. Org Biomol Chem. .

Abstract

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.

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