Presentation description

Prior to the advent of cross-coupling methodologies, amines were viewed as reliable templates for joining two molecules together. With cross-coupling technologies, two molecules can be readily linked together by C-C bond formation. Amine-derived electrophiles (C-N) bonds could be utilized for the synthesis of dimethylbiaryl atropisomeric cores found in complex natural products. In this project, we use amines to build successive C-C bonds by reductive cyclization and deaminative reactions. Intermediate amines are used as reliable handles for joining two molecular scaffolds together by reductive amination and substitution reactions. The amine intermediates are also precursors for chiral resolution by diastereomeric salt formation. Finally, post-cyclization amine removal (deamination) would provide access to dimethylbiaryl atropisomeric molecules.