Synthesis of diazadioxocalix[2]aren[2]triazine and tetraazacyclophane based new chiral catalysts and their use in stereoselective reactions

Asymmetric synthesis is a form of synthesis that allows the formation of chiral compounds selectively. Asymmetric synthesis is very important in organic chemistry, and this form of synthesis is widely used in the pharmaceutical and food industries. Because enantiomers or diastereomers of an organic molecule generally show different biological activities. In this study, novel efficient chiral diazadioxocalix[2]arene[2]triazine and tetraazacyclophane based organocatalysts have been designed and synthesized from the reaction of R/S-phenylethylamine with diazadioxocalix[2]arene[2]triazine and tetraazacyclophane. The synthesized novel diazadioxocalix[2]arene[2]triazine-based organocatalysts, were used in the addition to various aromatic trans‐β‐nitrostyrenes of acetylacetone, which is the enantioselective Michael reaction. As a result of the reactions, Michael products were obtained with high yields and enantioselectivites (up to 96% yield and 98% ee). In similarly, the synthesized novel tetraazacyclophane-based organocatalysts, were used in the addition to various aromatic benzaldehydes of acetone, which is the enantioselective Aldol reaction. As a result of the reactions, Aldol products were obtained with high yields and enantioselectivites (up to 95% yield and 97% ee). The structures of the synthesized compounds were identified by methods such as FT-IR, NMR, elemental analysis and optical rotation angle measurements. The enantiomeric excesses of the obtained Michael and Aldol products were determined by HPLC method.