Wang Resin-supported Enantioselective Catalysts for the Asymmetric Michael Additions ofAcetone to β-Nitroolefins

doi:10.1007/s40242-018-7189-z

高等学校化学研究 ›› 2018, Vol. 34 ›› Issue (1): 84-89.doi: 10.1007/s40242-018-7189-z

Wang Resin-supported Enantioselective Catalysts for the Asymmetric Michael Additions ofAcetone to β-Nitroolefins

SU Yuhan^1,2, QI Xuefei^1,2, TIAN Jun^1,2, LIN Chenhui^1,2, CHEN Ligong^1,2,3, LI Yang^1,2,3, JIN Yuehua⁴, YAN Xilong^1,2,3, WANG Bowei^1,2

1. School of Chemical Engineering and Technology, Tianjin University, Tianjin 300350, P. R. China;
2. Collaborative Innovation Center of Chemical Science and Engineering(Tianjin), Tianjin University, Tianjin 300350, P. R. China;
3. Tianjin Engineering Research Center of Functional Chemicals, Tianjin University, Tianjin 300350, P. R. China;
4. Tianjin Bohai Fine Chemical Co., Ltd., Tianjin 300300, P. R. China

收稿日期:2017-05-24 出版日期:2018-02-01 发布日期:2018-01-20
通讯作者: YAN Xilong,E-mail:yan@tju.edu.cn;WANG Boweim,E-mail:bwwang@tju.edu.cn E-mail:yan@tju.edu.cn;bwwang@tju.edu.cn
基金资助:
Supportted by the National Natural Science Foundation of China(No.21476163).

Wang Resin-supported Enantioselective Catalysts for the Asymmetric Michael Additions ofAcetone to β-Nitroolefins

SU Yuhan^1,2, QI Xuefei^1,2, TIAN Jun^1,2, LIN Chenhui^1,2, CHEN Ligong^1,2,3, LI Yang^1,2,3, JIN Yuehua⁴, YAN Xilong^1,2,3, WANG Bowei^1,2

1. School of Chemical Engineering and Technology, Tianjin University, Tianjin 300350, P. R. China;
2. Collaborative Innovation Center of Chemical Science and Engineering(Tianjin), Tianjin University, Tianjin 300350, P. R. China;
3. Tianjin Engineering Research Center of Functional Chemicals, Tianjin University, Tianjin 300350, P. R. China;
4. Tianjin Bohai Fine Chemical Co., Ltd., Tianjin 300300, P. R. China

Received:2017-05-24 Online:2018-02-01 Published:2018-01-20
Contact: YAN Xilong,E-mail:yan@tju.edu.cn;WANG Boweim,E-mail:bwwang@tju.edu.cn E-mail:yan@tju.edu.cn;bwwang@tju.edu.cn
Supported by:
Supportted by the National Natural Science Foundation of China(No.21476163).

摘要/Abstract

摘要： 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 trimesoyl 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-nitroolefins and excellent enantioselectivities(91.9% to 99.9%) were achieved.

关键词: Asymmetric Michael addition, (1R, 2R)-(+)-1, 2-DPEN, Immobilization, Enantioselectivity

Abstract: 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 trimesoyl 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-nitroolefins and excellent enantioselectivities(91.9% to 99.9%) were achieved.

Key words: Asymmetric Michael addition, (1R,2R)-(+)-1,2-DPEN, Immobilization, Enantioselectivity

SU Yuhan, QI Xuefei, TIAN Jun, LIN Chenhui, CHEN Ligong, LI Yang, JIN Yuehua, YAN Xilong, WANG Bowei. Wang Resin-supported Enantioselective Catalysts for the Asymmetric Michael Additions ofAcetone to β-Nitroolefins[J]. 高等学校化学研究, 2018, 34(1): 84-89.

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Wang Resin-supported Enantioselective Catalysts for the Asymmetric Michael Additions ofAcetone to β-Nitroolefins

Wang Resin-supported Enantioselective Catalysts for the Asymmetric Michael Additions ofAcetone to β-Nitroolefins

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