Nucleophilic Carbenes in Asymmetric Organocatalysis
Dieter Enders
* and Tim Balensiefer
Institute of Organic Chemistry, Technical University of Aachen, Professor-Pirlet-Strasse 1, 52074 Aachen, Germany
Acc. Chem. Res., 2004, 37 (8), pp 534–541
DOI: 10.1021/ar030050j
Publication Date (Web): March 25, 2004
Copyright © 2004 American Chemical Society
* Corresponding author. Phone: +49-241-8094676; fax: +49-241-8092-127; e-mail: enders@rwth-aachen.de.
Dieter Enders was born in 1946 in Butzbach, Germany. He studied chemistry at the Justus Liebig Universität Giessen and received his Dr. Rer. Nat. in 1974 under the supervision of Prof. Dieter Seebach. After postdoctoral studies at Harvard University with Prof. E. J. Corey, he went back to Giessen and obtained his habilitation in 1979. In 1980 he moved to the Universität Bonn as an associate professor before he changed again in 1985 to his present position as Professor of Organic Chemistry at the Rheinisch-Westfälische Technische Hochschule Aachen. He received many awards, among them the Prize of the Justus Liebig Universität Giessen (1978), the Leibniz Award (Deutsche Forschungsgemeinschaft, 1993), the Yamada Prize (Japan, 1995), the Max-Planck Research Award (Alexander von Humboldt- and Max-Planck-Gesellschaft, 2000), and the Emil Fischer Medal (Gesellschaft Deutscher Chemiker, 2002). His current research interests are asymmetric synthesis, especially the stereoselective synthesis of biologically active compounds, nucleophilic carbenes, and new synthetic methods using organometallics.
Tim Balensiefer was born in 1975 in Berlin, Germany. In 2002, he received his diploma degree in chemistry from the Rheinisch-Westfälische Technische Hochschule Aachen. He joined the group of Prof. Dieter Enders, where he is currently working on his Ph.D. in the research areas of nucleophilic carbenes and asymmetric organocatalysis.
Abstract
The coenzyme thiamine (vitamin B1), a natural thiazolium salt, is involved in many enzymatic catalyses. Since it has been proposed that the catalytically active species of these reactions is a nucleophilic carbene, many chemists have tried to perform enzyme mimetic asymmetric carbene catalysis. After a long and difficult search, stable carbenes are finally isolated, characterized, and in the chemist's hands. The experiments of decades have finally resulted in successful enantioselective benzoin condensations and enantioselective intramolecular Stetter reactions as important examples of carbene catalyzed asymmetric nucleophilic acylation processes.
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