The Application Of The Chiral Cyclohexanediamine Derivatives In Asymmetric Knoevenagel Reaction

Knoevenagel consendation reaction is processed between aldehydes or ketones and active methylene compounds. The reaction is used for the synthesis of ?, ?-unsaturated carbonyl compounds and is an important synthetic method for forming carbon=carbon double bonds in organic synthesis. Regardless of its comprehensive reports and applications, the research on asymmetric Knoevenagel condensation reaction is seldom reported. This thesis mainly focuses on synthesizing a variety of the chiral cyclohexanediamine derivatives catalysts from trans-1, 2-cyclohexanediamine and particularly studied about its applications in asymmetric Knoevenagel condensation reaction as follows:A lot of routes to prepare chiral cyclohecxanediamines catalysts were reported: trans-1, 2-cyclohexanediamines as raw material, through acylation, Schiff base, reduction and alkylation reaction to synthesize various chiral cyclohexanediamines derivatives with high yield. The structures of the products were represented by ~1H NMR and MS.The synthesis of 2-phenyl propanal and 2-phenyl butyraldehyde derivatives--the substrates of asymmetric Knoevenagel condensation was studied, through the Darzens condensation or Corey epoxidation reaction. By single factor experiment, the optimum reaction conditions were determined, and the products structure was detected by ~1H NMR.The chiral cyclohexanediamines catalysts was used in asymmetric Knoevenagel condensation reaction, with the reaction of 2-phenyl propanal and diethylmalonate as a model, through the single factor experiment of catalyst, amount of catalyst, solvent and reaction temperature to determine the optimal reaction conditions are studied. And under this optimum condition to the Knoevenagel condensation, a variety of different desired products were obtained. The products were determined by ~1H NMR, 13 C NMR, MS and chiral HPLC.