Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (6): 1218-1221.DOI: 10.6023/cjoc201401019 Previous Articles     Next Articles



赵云辉, 任新芳, 刘汉文, 唐子龙   

  1. a. 湖南科技大学化学化工学院 湘潭 411201;
    b. 理论化学与分子模拟省部共建教育部重点实验室 湘潭 411201
  • 收稿日期:2014-01-11 修回日期:2014-02-12 发布日期:2014-03-10
  • 通讯作者: 赵云辉, 刘汉文;
  • 基金资助:

    国家自然科学基金(No. 21372070)、湖南省科学基金课题(No. 11JJ3016)和湖南省教育厅基金(No. B31314)资助项目.

Study on Synthesis of ortho-Hydroxyl Aromatic N-tert-Butylsulfinyl Imines under Microwave Irradiation

Zhao Yunhui, Ren Xinfang, Liu Hanwen, Tang Zilong   

  1. a. School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201, China;
    b. Key Laboratory of Theoretical Chemistry and Molecular Simulation of Ministry of Education of China, Human University of Science and Technology, Xiangtan 411201, China
  • Received:2014-01-11 Revised:2014-02-12 Published:2014-03-10
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21372070), the Science Foundation of Hunan Province (No. 11JJ3016) and the Hunan Provincial Education Office Scientific Research Foundation Project (No. B31314).

Chiral N-tert-butanesulfinyl imines have been shown to be important intermediates for asymmetric synthesis in recent years. Eleven new (R,E)-N-(2-hydroxybenzylidene)-tert-butyl-sulfinamides (3) were synthesized from salicylaldehydes 1 and chiral tert-butanesulfinamide 2 under microwave irradiation in moderate to good yields. The reaction could work well in the mixture of KHSO4/PhMe or Cs2CO3/CH2Cl2. And the results show that the KHSO4/PhMe reaction system is helpful for the salicylaldehydes with electron-donating group; however, the Cs2CO3/CH2Cl2 reaction system is applicable to the salicylaldehydes with electron-deficient group and steric hindrance group. The structures of these new compounds were determined by 1H NMR, 13C NMR, IR and HRMS.

Key words: microwave irradiation, chiral imine, (R)-tert-butylsulfinamide, salicylaldehyde