Amino-alcohols are frequently used in medicinal chemistry and in the design of ligands for asymmetric catalysis. The derivatization of this important class of compounds is thus of prime interest. Organobismuth reagents have found increasing use in organic synthesis due to the low cost and low toxicity associated with bismuth salts. Because of the relative weakness of the carbon-bismuth bond, these organometallic reagents possess a unique reactivity that can be advantageously utilized in the design of new reactions. In this presentation, our latest results in the development of copper-catalyzed arylation reactions of amino-alcohols will be presented. An interesting directing effect by a properly located group will be illustrated. Application of this reaction in the arylation of tryptophanol and tryptophan derivatives will be discussed.

Investigation into the directed copper-catalyzed O-arylation reaction of amino-alcohols

248th National Meeting (2014)

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