Synthesis of Optically Active Cyclam and Its Transformations

Cyclam is a well-known example of a polyaza macrocycle. However, there are few reports of its optically active versions. In this study, we synthesized highly symmetric optically active cyclam (S,S,S,S)-5,7,12,14-tetraphenyl-1,4,8,11-tetraazacyclotetradecane, which has four phenyl groups on the cyclam skeleton, and derivatized it in various ways. We were able to synthesize a chiral Cu complex, an N-ethyl derivative, and a dithiourea from this optically active cyclam. The structures of the chiral Cu complex and dithiourea were verified by single-crystal X-ray diffraction analysis.