Design, Synthesis, And Evaluation Of C2-Symmetric Diamines For Asymmetric Synthesis

Chiral diamines play an important role in asymmetric synthetic transformations. (-)-Sparteine is one such diamine; however, its commercial availability has become limited over the last ten years. In light of this, the development of sparteine surrogates has been of interest to the synthetic chemistry community. The following work describes the design, synthesis, and evaluation of three generations of potential sparteine surrogates. The metal ligating ability of these diamines was studied, and their value in asymmetric synthesis was investigated. Additionally, incorporation of one of the diamines into a tetraazamacrocyclic framework was achieved. This tetraazamacrocycle has potential to be used for the development of enantioselective atom transfer processes, i.e. epoxidation, aziridination, or cyclopropanation.