The Research Of Organic Amine Catalyze Asymmetric Reactions And Green Methods To Synthesize Pyrrole, Quinoline Derivatives

An acidic ionic liquid, [BSO3HMIm]HSO4, was used as an efficient catalyst for the synthesis of a variety of pyrrole derivatives via a one-pot, three-component condensation of amines, nitroolefins, and 1,3-dicarbonyl compounds. Good to excellent yields of 72-96% were obtained under reflux in ethanol. The catalyst could easily be recovered and recycled up to six times resulting in good yields without prolonging the reaction time. This method was also efficient in large-scale preparation. The procedure could be easily expanded to a one-pot, four-component reaction. This ionic liquid-catalyzed reaction provided an environmentally friendly alternative to the synthesis of pyrrole derivatives.A facile and efficient method enabling the construction of quinoline dicarboxylic esters was developed via the tandem reaction of arylamines, ethyl glyoxylate and a-ketoesters under the catalysis of iodine and mediation of ambient oxygen. Various arylamines and a-ketoesters could participate in the reaction, and the desired products were obtained in yields of up to 92%. Iodine, an easily available, environmentally benign and inexpensive catalyst, made it more accessible to prepare various substituted quinoline-2,4-dicarboxylates through this tandem reaction.A highly efficient, bifunctional prolinamide catalyst, which consists of chiral proline and trans-cyclohexanediamine moieties, was prepared and evaluated in direct asymmetric aldol reactions of various ketones and aldehydes. The catalyst displayed impressive catalytic activity towards heterocyclic ketones containing oxygen, sulfur, or nitrogen which have not yet been sufficiently explored. With heterocyclic ketones or cyclohexanone, the aldol reactions gave products in high yields with respectable enantioselectivities (87%-99% ee) and diastereoselectivities (up to>99:1 anti syn). The catalyst could be recycled and reused up to seven times resulting in good yields with good selectivities. This catalyst is also efficient in large-scale reactions with the enantioselectivities maintaining at the same level as in experimental scale reactions.A simple organocatalytic Michael-aldol-dehydration domino approach to chiral 3,5-diaryl-cyclohexenones from acetone and chalcones was developed for the first time using a simple chiral primary amine as a catalyst. Moderate to good yields (up to 85%) and excellent enantioselectivities (91-98% ee) were obtained.Prolinamide catalysts are widely used in asymmetric aldol reactions. However, the use of prolinamide to catalyze the domino reaction was reported rarely. We report the domino reaction of 1,4-dithiane-2,5-diol with cinnamaldehydes for synthesis of functionalized dihydrothiophenes with good yields (up to 84%) and enantioselectivities (up to 92%) catalyzed by prolinamide catalyst.