Intramolecular Hydroamination of Alkynes Catalyzed by Silver-Phenanthroline Complexes

The intramolecular hydroamination reaction is among the more versatile means of forming nitrogen-containing hetereocycles, compounds of interest in a variety of chemical disciplines. While the reaction has been intensely studied, concerns still exist over its amenability to organic synthesis. This thesis details the implementation of a readily-recyclable silver-1,10-phenanthroline catalyst which has demonstrated high efficiency for the hydroamination of a variety of aminoalkynes. As a means for developing a protocol for enantioselective synthesis, the desymmetrization of a prochiral diyne was accomplished using the silver-1,10-phenanthroline catalyst. This desymmetrization creates chiral compounds, an occurrence not often observed in the alkyne hydroamination.

A separate project involved in the development of improved immunotherapies led us to develop and complete a synthesis of β-hydroxy-methionine. The third attempt via vinyl glycine eventually allowed for the completion of this molecule. It is planned for this amino acid derivative to be included in an antigenic peptide.