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Synthesis 2011(2): 190-198  
DOI: 10.1055/s-0030-1258363
FEATUREARTICLE
© Georg Thieme Verlag Stuttgart ˙ New York

Chemoselective Crossed Acyloin Condensations: Catalyst and Substrate Control

Christopher A. Rosea, Sivaji Gundalab, Stephen J. Connon*b, Kirsten Zeitler*a
a Institut für Organische Chemie, Universität Regensburg, Universitätsstrasse 31, 93053 Regensburg, Germany
Fax: +49(941)9434121; e-Mail: kirsten.zeitler@chemie.uni-regensburg.de;
b Centre for Synthesis and Chemical Biology, School of Chemistry, The University of Dublin, Trinity College, Dublin 2, Ireland
Fax: +353(167)12826; e-Mail: connons@tcd.ie;
Further Information

Publication History

Received 17 November 2010
Publication Date:
20 December 2010 (online)

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Abstract

The interplay between catalyst and substrate control in crossed acyloin condensation reactions has been studied. It was found that a pentafluorophenyl-substituted triazolium ion derived catalyst was capable of catalyzing highly chemoselective processes between a range of aliphatic and aromatic aldehydes utilized in a 1:1 ratio.

Key words

organic synthesis - carbenes - heterocycles - catalysis - umpolung reactions

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21

In order to reproduce the conditions on a smaller scale we found a tube-shaped flask better suited to handle smaller amounts of solvent [cf. high concentration of the reactions performed by Stetter (ca. 3 M)].