Two Wang resin-supported （1R,2R）-（＋）-1,2-DPEN（DPEN=diphenylethylenediamine） catalysts were synthesized from cyanuric chloride and trimesoyl chloride, respectively. These two catalysts were characterized by FTIR...Two Wang resin-supported （1R,2R）-（＋）-1,2-DPEN（DPEN=diphenylethylenediamine） catalysts were synthesized from cyanuric chloride and trimesoyl chloride, respectively. These two catalysts were characterized by FTIR, TGA and elemental analysis. The results demonstrated that （1R,2R）-（＋）-1,2-DPEN was successfully bonded to the surface of Wang resin through the amido linkage. Subsequently, the asymmetric Michael addition of acetone to β-nitrostyrene was employed to evaluate their catalytic performance. It was found that the catalyst generated from trilnesoyl chloride exhibited much better catalytic behavior than our previously reported catalyst, likely attributed to the multiple hydrogen-bond interaction between β-nitrostyrene and amide group, which made the catalytic transition intermediates more stable. Under the optimal conditions, 76.1% β-nitrostyrene conversion and 93.8% enantioselectivity were obtained. Finally, the generality of this catalyst was examined with Michael additions of acetone to β-nitroolefms and excellent enantioselectivities（91.9% to 99.9%） were achieved.展开更多
基金Supportted by the National Natural Science Foundation of China（No.21476163）.
文摘Two Wang resin-supported （1R,2R）-（＋）-1,2-DPEN（DPEN=diphenylethylenediamine） catalysts were synthesized from cyanuric chloride and trimesoyl chloride, respectively. These two catalysts were characterized by FTIR, TGA and elemental analysis. The results demonstrated that （1R,2R）-（＋）-1,2-DPEN was successfully bonded to the surface of Wang resin through the amido linkage. Subsequently, the asymmetric Michael addition of acetone to β-nitrostyrene was employed to evaluate their catalytic performance. It was found that the catalyst generated from trilnesoyl chloride exhibited much better catalytic behavior than our previously reported catalyst, likely attributed to the multiple hydrogen-bond interaction between β-nitrostyrene and amide group, which made the catalytic transition intermediates more stable. Under the optimal conditions, 76.1% β-nitrostyrene conversion and 93.8% enantioselectivity were obtained. Finally, the generality of this catalyst was examined with Michael additions of acetone to β-nitroolefms and excellent enantioselectivities（91.9% to 99.9%） were achieved.
