Issue 19, 2012
From the journal:

Organic & Biomolecular Chemistry

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

Nicholas J. Bennett,a   Mark C. Elliott,*b   Natalie L. Hewitt,b   Benson M. Kariuki,b   Clare A. Morton,b   Steven A. Rawc  and  Simone Tomasic  

* Corresponding authors

a Chemistry Department, AstraZeneca R&D Charnwood, Bakewell Road, Loughborough, UK

b School of Chemistry, Cardiff University, Park Place, Cardiff, UK
E-mail: elliottmc@cardiff.ac.uk
Fax: +44(0)29 20874030
Tel: +44(0)29 20874686

c AstraZeneca, Medicines Evaluation Chemistry, Pharmaceutical Development, Silk Road Business Park, Charter Way, Macclesfield, Cheshire, UK

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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Article information

DOI
https://doi.org/10.1039/C2OB25211B
Article type
Paper
Submitted
27 Jan 2012
Accepted
22 Mar 2012
First published
23 Mar 2012

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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