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
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.