Issue 5, 2008
From the journal:

Chemical Communications

Organocatalytic asymmetric vinylogous addition to quinones – formation of optically active α-aryl ketones†

José Alemán,a   Christian Borch Jacobsen,a   Kim Frisch,a   Jacob Overgaarda  and  Karl Anker Jørgensen*a  

* Corresponding authors

a Danish National Research Foundation: Center for Catalysis, Department of Chemistry, Aarhus University, Denmark
E-mail: kaj@chem.au.dk
Fax: +45 8619 6199
Tel: +45 8942 3910

Abstract

The first organocatalytic addition of dicyanoalkylidenes to quinones catalyzed by Cinchona alkaloids leading to formation of 1,4-diketone derivatives with high diastereomeric ratios (up to >98 : <2 dr) and enantioselectivities (up to 99% ee) has been developed; the optically active compounds obtained are useful for a number of transformations, e.g. the synthesis of optically active α-aryl ketones.

Graphical abstract: Organocatalytic asymmetric vinylogous addition to quinones – formation of optically active α-aryl ketones

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Article information

DOI
https://doi.org/10.1039/B716485H
Article type
Communication
Submitted
26 Oct 2007
Accepted
15 Nov 2007
First published
28 Nov 2007

Chem. Commun., 2008, 632-634

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Organocatalytic asymmetric vinylogous addition to quinones – formation of optically active α-aryl ketones

J. Alemán, C. B. Jacobsen, K. Frisch, J. Overgaard and K. A. Jørgensen, Chem. Commun., 2008, 632 DOI: 10.1039/B716485H

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