Synthesis of new organocatalysts derived from bile acids and their use in aqueous solvent

Bile acids are a very important class of natural surfactants, showing themselves and their derivatives as self-assembling materials. The morphology of the aggregates is dependent upon the substituents present both on the rigid steroid backbone and on the side chain. For this reason, they are very suitable for nanochemistry, sensing and drug delivery applications. In the last years, our group has been involved in a project concerning the preparation of bile acid derivatives bearing amino acid moieties either on the C-3 or on the lateral chain of the steroid polycyclic ring. Click chemistry approach was also used as useful method to link the steroid backbone to different aromatic units, such as naphthalene and anthracene, which could be good lipophilic “solvents” for the reagents used in the organocatalized reactions in aqueous solutions. Our interest in conducting water-catalyzed organoreactions stems from the fact that water is the green solvent “par excellence” and it has been proved that it accelerates the rates of many reactions. In this work, we present a variety of organocatalysts derived from bile acid bearing amino acid moieties, which we subsequentially have tested in aldolic reactions in water.