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Pure Appl. Chem., 2010, Vol. 82, No. 7, pp. 1529-1536

Published online 2010-05-02

Combined coinage metal catalysis for the synthesis of bioactive molecules

Norbert Krause*, Özge Aksin-Artok, Viola Breker, Carl Deutsch, Birgit Gockel, Manojkumar Poonoth, Yoshinari Sawama, Yuka Sawama, Tao Sun and Christian Winter

Department of Organic Chemistry, Dortmund University of Technology, Otto-Hahn-Strasse 6, D-44227 Dortmund, Germany

Abstract: The use of the coinage metals copper, silver, and gold enables an efficient and stereo-selective assembly of bioactive heterocycles via allenic intermediates. The synthesis of functionalized allenes by SN2'-substitution or SN2'-reduction is mediated or catalyzed by copper, whereas silver and gold are the catalysts of choice for subsequent 5- or 6-endo-cyclizations. Overall, this sequence proceeds with efficient center-to-axis-to-center chirality transfer.