Novel supramolecular organocatalysts of hydroxyprolinamide based on calix[4]arene scaffold for the enantioselective Biginelli reaction  

作　　者：LI ZhengYi XING HuaiJie HUANG GuoLi SUN XiaoQiang JIANG JuLi WANG LeYong 

机构地区：[1]Key Laboratory of Fine Petrochemical Engineering, School of Petrochemical Engineering, Changzhou University Changzhou 213164, China [2]Institute of Chemical Biology and Drug Innovation, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, China

出　　处：《Science China Chemistry》2011年第11期1726-1734,共9页中国科学（化学英文版）

基　　金：financial support from the National Natural Science Foundation of China (21002009, 21072093 & 20872051);the Doctoral Fund of Ministry of Education of China (20090091110017);Priority Academic Program Development of Jiangsu Higher Education Institutions;also supported by the Fundamental Research Funds for the Central Universities (1107020526 & 1103020505)

摘　　要：A series of novel supramolecular organocatalysts of hydroxyprolinamide based on the upper rim of calix[4]arene scaffold have been developed to catalyze enantioselective multi-component Biginelli reaction. Under the optimal conditions, the reactions occurred with moderate-to-excellent enantioselectivities (up to 98% ee). A plausible transition state constructed by the supra- molecular interaction of hydrogen bond and cation-π between catalysts and substrates has been proposed.A series of novel supramolecular organocatalysts of hydroxyprolinamide based on the upper rim of calix[4]arene scaffold have been developed to catalyze enantioselective multi-component Biginelli reaction. Under the optimal conditions, the reactions occurred with moderate-to-excellent enantioselectivities （up to 98% ee）. A plausible transition state constructed by the supramolecular interaction of hydrogen bond and cation-π between catalysts and substrates has been proposed.

关 键 词：supramolecular organocatalyst CALIX[4]ARENE hydroxyprolinamide enantioselective Biginelli reaction 

分 类 号：O626.41[理学—有机化学] TQ324.9[理学—化学]