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Issue 19, 2012
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Diastereoselective alkylation reactions of 1-methylcyclohexa-2,5-diene-1-carboxylic acid

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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.

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

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Publication details

The article was received on 27 Jan 2012, accepted on 22 Mar 2012 and first published on 23 Mar 2012


Article type: Paper
DOI: 10.1039/C2OB25211B
Citation: Org. Biomol. Chem., 2012,10, 3859-3865
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    Diastereoselective alkylation reactions of 1-methylcyclohexa-2,5-diene-1-carboxylic acid

    N. J. Bennett, M. C. Elliott, N. L. Hewitt, B. M. Kariuki, C. A. Morton, S. A. Raw and S. Tomasi, Org. Biomol. Chem., 2012, 10, 3859
    DOI: 10.1039/C2OB25211B

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