Issue 7, 2008
From the journal:

Organic & Biomolecular Chemistry

In situ generation of Mes2Mg as a non-nucleophilic carbon-centred base reagent for the efficient one-pot conversion of ketones to silyl enol ethers

William J. Kerr,*a   Allan J. B. Watsona  and  Douglas Hayesb  

* Corresponding authors

a Department of Pure and Applied Chemistry, WestCHEM, University of Strathclyde, 295 Cathedral Street, Glasgow, Scotland, UK
E-mail: w.kerr@strath.ac.uk
Fax: +44 141 548 4246
Tel: +44 141 548 2959

b GlaxoSmithKline, Medicines Research Centre, Gunnels Wood Road, Stevenage, Hertfordshire, UK

Abstract

Treatment of commercially available MesMgBr with 1,4-dioxane produces the key Mes2Mg reagent in situ which then mediates the deprotonation of ketones to deliver trimethylsilyl enol ethers, at readily accessible temperatures and without any nucleophilic addition, in an expedient and high yielding one-pot process.

Graphical abstract: In situ generation of Mes2Mg as a non-nucleophilic carbon-centred base reagent for the efficient one-pot conversion of ketones to silyl enol ethers

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Article information

DOI
https://doi.org/10.1039/B802082E
Article type
Paper
Submitted
05 Feb 2008
Accepted
11 Feb 2008
First published
25 Feb 2008

Org. Biomol. Chem., 2008,6, 1238-1243

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In situ generation of Mes2Mg as a non-nucleophilic carbon-centred base reagent for the efficient one-pot conversion of ketones to silyl enol ethers

W. J. Kerr, A. J. B. Watson and D. Hayes, Org. Biomol. Chem., 2008, 6, 1238 DOI: 10.1039/B802082E

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