Combined coinage metal catalysis for the synthesis of bioactive molecules

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

doi:10.1351/PAC-CON-09-09-23

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

http://dx.doi.org/10.1351/PAC-CON-09-09-23

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 S_N2'-substitution or S_N2'-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.