A major obstacle in drug design today is the issue of axial chirality, which typically arises from hindered rotation around an sp2-sp2 bond. We have set out to develop new chemical methodologies that enable the facile synthesis of atropisomeric amides, which are ubiquitous throughout biologically active small molecules. The overarching goal is to develop an atropisomer selective amide coupling between a carboxylic acid and an amine. This master's thesis will discuss a diverse set of methods that we have studied towards this goal. Finally, in response to an accident in an undergraduate organic lab there was a need to update and replace a potentially dangerous 'classic' lab module. To this end we created a new lab module based on chemistry that was recently developed in the Gustafson lab. In the chlorination of caffeine through the use of a Lewis Base catalyst, students are introduced to electrophilic aromatic substitutions as well as modern concepts and techniques such as catalysis and chromatography. The lab module was successfully "beta tested" across two sections of Chemistry 432 in the Spring 2015 section at SDSU and will be extended to all sections in the oncoming semesters.
