It is one of the most attractive types of asymmetric synthesis that chiral commpounts are generated under the influence of chiral catalysts. In recent years catalytic asymmetric Michael addition by chiral metal complexes has been recognized as an efficient method for obtaining asymmetric products. In this work we reported that using potassium thiazolidine -2-thione-4-carboxylate [(R)-TTCA·K] as the chiral catalyst, the addition reaction of cyclohexanone with acrylonitrile was carried out and optically active (S)-(+)-2-cyanoethyl cyclohexanone 1 ([α] 20 D=+2.8°, e.e. 19%) and hydrolysis product of 1, (S)-(-)-2-oxocyclohexanepropionic acid 2 ([α] 20 D=-2.95°, e.e. 19%), were obtained. Enantiomeric excess of compound 1 was determined by resolution of (R,S)-2-oxocyclohexanepropionic acid with (-)-quinine. Compounds 1 and 2 were easily racemized at a long time for laying aside and in the presence of dil H 2SO 4 or dil base. When (S)-(+)-2-cyanoethyl cyclohexanone reacts with ethylene glycol in the presence of toluene sulfonic acid as the catalyst the racemic 2-ethylendioxy cyclohexyl propionitrile was obtained. The mechanism of the reaction of cyclohexanone with acrylonitrile would be a complicated catalysis process.
The esterification of carboxylic acid with alcohol in the presence of catalytic amounts of mineral acids is one of the most methods for preparing esters.The catalysts generally preferred are sulfuric acid or p-toluenesulfonic acid.But the products esters were racemic when（S）-3-（2′-oxocyclohexyl） propionic acid reacts with alcohols in the presence of sulfuric acid or with p-toluenesulfonic acid as catalyst.We replace sulfuric acid with Fe2(SO4)3·xH2O as the catalyst.The optical compound（S）-methyl-3-（2′-oxocyclohexyl）propionate,（（S）-ethyl-3-）（2′-oxocyclohexyl）propionate and（S）-n-butyl-3-（2′-oxocyclohexyl）propionate were obtained.In this paper we also reported that cyclohexanone reacted with methyl acrylate in the presence of potassium thiazolidine-2-thione-4-carboxylate（R）TTCA·K as the chiral catalyst to afford optically active（S）-3-（2′-oxocy-clohexyl） propionate.The mechanism of reaction of cyclohexanone with methyl acrylate in the presence of（R）TTCA·K as the catalyst would be a complex process.
