Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (5): 1520-1526.DOI: 10.6023/cjoc202111030 Previous Articles     Next Articles



马志伟a,*(), 陈晓培a, 王川川a, 王建玲a, 陶京朝b, 吕全建a,*()   

  1. a 河南牧业经济学院理学部 郑州 450046
    b 郑州大学化学学院 郑州 450001
  • 收稿日期:2021-11-22 修回日期:2022-01-02 发布日期:2022-01-20
  • 通讯作者: 马志伟, 吕全建
  • 作者简介:
  • 基金资助:
    河南省自然科学基金(202300410188); 河南省高等学校青年骨干教师培养计划(2021GGJS173)

Chiral Squaramide Catalyzed Enantioselective Michael Addition of Cyclic 1,3-Diketones to β,γ-Unsaturated α-Keto Esters

Zhiwei Maa(), Xiaopei Chena, Chuanchuan Wanga, Jianling Wanga, Jingchao Taob, Quanjian Lüa()   

  1. a Faculty of Science, Henan University of Animal Husbandry and Economy, Zhengzhou 450046
    b College of Chemistry, Zhengzhou University, Zhengzhou 450001
  • Received:2021-11-22 Revised:2022-01-02 Published:2022-01-20
  • Contact: Zhiwei Ma, Quanjian Lü
  • About author:
    These authors contributed equally to this work
  • Supported by:
    Natural Science Foundation of Henan Province(202300410188); Training Plan for Young Key Teachers in Colleges and Universities in Henan Province(2021GGJS173)

A stereoselective methodology was developed to construct synthetically and pharmaceutically useful chiral chromene derivatives. In the presence of a newly designed bifunctional tertiary amine-squaramide organocatalyst, the Michael addition between cyclic 1,3-diketones and β,γ-unsaturated α-ketoesters occurred smoothly to provide the desired products with high to excellent yields (84%~97%) and enantioselectivies (79%~97% ee). This catalytic protocol was compatible with a range of structurally distinct β,γ-unsaturated α-ketoesters.

Key words: Michael addition, organocatalysis, tertiary amine-squaramide, cyclic diketone, β,γ-unsaturated α-ketoesters