Investigation of activities of various organocatalysts in aminonitrile synthesis

α-Aminonitriles are useful acyl anion and iminium ion equivalents and also very versatile intermediates for the synthesis of α-amino acids, 1,2-diamines, various nitrogen containing heterocycles and several biologically active compounds. Three component reactions of aldehydes, amines and cyanide known as the Strecker reaction provides a traditional way to α-aminonitriles. Many modifications and catalysts have been developed to enhance the efficiency of the reaction. Asymmetric synthesis of α-aminonitriles have great importance in organic chemistry, because they are precursors of important compouns for biological systems. Two different strategies have been developed for their asymmetric synthesis. One of these strategies is using chiral axilary or precursor, the other one is using chiral catalysts. Recently, reserchers have focused on using chiral catalysts with or without metal and many researches have been done on this subject. In the first part of this research, optically pure five new bifunctional organocatalysts having urea and prolinamide structure have been synthesized. It was expected that these compounds would show asymmetric induction in tree component Strecker reaction via hidrogen bonding interaction. By this aim, the amidation reaction of 1-(phenylcarbamoyl)pyrrolidin-2-carboxylic acid, which was obtained from the reaction of L-prolin with phenylisocyanate, with amine, aminoalcohol and amino acid esters have been used. In the following part, activities of obtained organocatalysts in the synthesis of aminonitriles have been investigated under several conditions such as temperature, solvent and additive. It has been shown that the organocatalysts catalyzed the reaction with good yields, while they have not showed any significant asymmetric induction.