Development of Practical Synthetic Tools Using Copper and Gold Catalysis
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The use of transition metal catalysis in the synthesis of complex organic molecules has dramatically expanded the role of synthetic chemistry across a broad spectrum of applications including drug discovery, chemical biology, and materials science. This is due in large part to the development of practical, transition-metal-catalyzed techniques for: 1) the construction of synthetically challenging molecular structures and 2) the selective activation of strong bonds. Our contribution in the first area has focused on the functionalization of C-C multiple bonds using copper and gold catalysts. I will begin by discussing the development of a convenient method for the asymmetric synthesis of cyclic ethers containing highly-substituted stereocenters: complex structures which are found in a wide variety of natural products. Our efforts in the second area have been directed at C-O bond activation using copper catalysts. I will describe our investigation of the copper-catalyzed reduction of alkyl triflates, and how this technique was applied in a new approach to the selective deoxygenation of primary alcohols that offers significant advantages over traditional methods. Finally, I will present an extension of this strategy to the copper-catalyzed reduction of primary and secondary halides which proceeds through a non-radical mechanism.
- Chemistry