In summary, this work demonstrates the syntheses of 13 chiral hydrogen bond donor catalysts based on guanidines. Among them, it was possible to isolate nine potential guanidine-based catalysts. In general, four different approaches based on the use of thioureas, isothioureas, 2-chlorobenzimidazole and carbodiimides for the synthesis of these guanidines have been investigated. Chiral thiourea starting material, necessary for the first approach, has been prepared in seven steps following the synthesis strategy developed by our group. By reaction of these thioureas with an oxidising agent, like 2-iodoxybenzoic acid (IBX) or (diacetoxy)iodobenzene, two promising bifunctional guanidine-based catalysts carrying a quaternary ammonium group have been synthesised. In addition, the benzylation reaction of one of these guanidines succeeded. The second approach, starting from isothiourea, did not give any desired guanidine product and has therefore not been investigated further. In the course of the third approach using 2-chlorobenzimidazole, it was possible to obtain eight different guanidines. Among them, five have been isolated and were available for subsequent test reactions. Finally, syntheses starting from carbodiimides have also been examined, resulting in the successful synthesis of two chiral bifunctional catalysts based on guanidines. To investigate the applicability of these newly developed catalysts, they were subjected to a series of test reactions.