Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (4): 1053-1063.DOI: 10.6023/cjoc201809015 Previous Articles     Next Articles

Articles

手性硫脲-酰胺催化1,3-二酮对硝基烯烃的不对称Michael加成反应

白冰a, 王龙a, 杨静a, 蔡莉莉b, 刘前进b, 席高磊b, 赵志伟b, 毛多斌a, 陈芝飞b   

  1. a 郑州轻工业学院 食品与生物工程学院 郑州 450000;
    b 河南中烟工业有限责任公司技术中心 郑州 450000
  • 收稿日期:2018-09-10 修回日期:2018-11-14 出版日期:2019-04-25 发布日期:2018-12-28
  • 通讯作者: 毛多斌, 陈芝飞 E-mail:maoduobin@sohu.com;chenzhifei@126.com
  • 基金资助:

    河南省科技厅(No.172102210068)、郑州轻工业学院(No.2013BSJJ009)资助项目.

Asymmetric Conjugate Addition of 1,3-Diketone to Nitroalkenes Catalyzed by Bifunctional Thiourea-Amide Organocatalysts

Bai Binga, Wang Longa, Yang Jinga, Cai Lilib, Liu Qianjinb, Xi Gaoleib, Zhao Zhiweib, Mao Duobina, Chen Zhifeib   

  1. a School of Food & Biological Engineering, Zhengzhou University of Light Industry, Zhengzhou 450000;
    b Technology Center, China Tobacco Henan Industrial Co., Ltd., Zhengzhou 450000
  • Received:2018-09-10 Revised:2018-11-14 Online:2019-04-25 Published:2018-12-28
  • Contact: 10.6023/cjoc201809015 E-mail:maoduobin@sohu.com;chenzhifei@126.com
  • Supported by:

    Project supported by the Department of Science and Technology of Henan Province (No.172102210068) and the Zhengzhou University of Light Industry (No.2013BSJJ009).

New bifunctional chiral thiourea-amide organocatalysts were developed. Their applications in asymmetric conjugate addition of 2,4-pentandione to various nitroalkenes were investigated. The corresponding adducts were obtained in excellent yields with high enantioselectivities up to 94% ee in present of 1 mol% catalyst. The catalytic system could also suit for various nitroalkenes bearing electron-donating or electron-withdrawing groups. The preliminary structure-activity relationship study reveals that the acyl group in pyrrolidine N position plays an important role in catalyzing the reaction.

Key words: thiourea-amide, organocatalyst, Michael addition, asymmetric