We describe herein a route to novel oligomeric structures containing a Tröger’s base-derived core that are linked through phenazine rings, as indicated in octamer <b>I</b>. Computational modeling reveals that these structures adopt helical conformations where the absolute stereochemistry of the monomer controls the orientation of the three-dimensional helical structure. The synthesis of these compounds is based on methodology developed in our laboratory for the synthesis of highly substituted phenazines via double Buchwald-Hartwig coupling.<br/><br/>We also describe an approach to the non-covalent assembly of helical systems in which a Tröger’s base monomer is organized about a tetrahedral metal center. The application of these systems to the development of dynamic combinatorial libraries will be discussed.

Synthesis of novel Tröger’s base derived helical scaffolds

252nd National Meeting (2016)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.