Chiral ynamides (Figure1) are a useful functional group in organic synthesis. They are capable of undergoing regio- and stereoselective transformations. In addition, they are stable and easily handled.

While the Hsung group and others have established the utility of chiral ynamides in organic synthesis, to date, no one has tested the durability, or survivability, of these functional groups. This is the goal of my research project. So far, completed work includes the four-step synthesis of a chiral auxiliary (Figure 2). I also have successfully synthesized an ynamide substrate (Figure 3) bearing a protected alcohol. In addition, deprotection of the alcohol, oxidation of the hydroxyl group, and Wittig olefination have also been completed. Experiments including Grignard reaction, Horner-Wadsworth-Emmons olefination, [1,4] addition, reduction, oxidation, protection and deprotection serve as a few examples of reactions that may be carried out in the presence of the ynamide functional group.

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