有机化学 ›› 2017, Vol. 37 ›› Issue (10): 2685-2689.DOI: 10.6023/cjoc201703001 上一篇    下一篇

研究论文

一类具有C2对称性的轴手性马来酰亚胺类化合物的合成

符立言a,b, 吉保明a, 杜晨霞b   

  1. a 洛阳师范学院化学化工学院 洛阳 471022;
    b 郑州大学化学与分子工程学院 郑州 450001
  • 收稿日期:2017-03-01 修回日期:2017-06-07 出版日期:2017-10-25 发布日期:2017-06-23
  • 通讯作者: 吉保明 E-mail:lyhxxjbm@126.com
  • 基金资助:

    国家自然科学基金(No.21372112)资助项目.

Synthesis of a New Class of Chiral Maleimide Derivatives with C2-Symmetry

Fu Liyana,b, Ji Baominga, Du Chenxiab   

  1. a College of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang 471022;
    b College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450001
  • Received:2017-03-01 Revised:2017-06-07 Online:2017-10-25 Published:2017-06-23
  • Contact: 10.6023/cjoc201703001 E-mail:lyhxxjbm@126.com
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No.21372112).

以廉价易得的顺丁烯二酸酐和(R)-1,1'-联二萘酚(BINOL)为起始原料,通过Williamson醚合成法、Suzuki偶联反应、脱保护基等6步反应,以6.2%~16%的总收率合成了一类具有C2对称性的轴手性酰亚胺类化合物,并通过1H NMR,13C NMR,HRMS,IR等手段对其结构进行了表征.

关键词: 酰亚胺, 联萘酚, 有机合成, 手性

Starting from the readily available maleic anhydride and (R)-1,1'-bi-2-naphthol (BINOL), an efficient method for the synthesis of a new class of chiral maleimide derivatives with C2-symmetry was described, involving Williamson ether synthesis, Suzuki coupling reaction and deprotection reaction by microwave to give 3,4-[(R)-3,3'-diaryl-1,1'-binaphthyl-2,2'-dioxy]-maleimides in 6.2%~16% yields. Moreover, the structures of the target compound and key intermediates were confirmed by 1H NMR, 13C NMR, HRMS and IR techniques.

Key words: imide, BINOL, organic synthesis, chirality