Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (6): 1177-1182.DOI: 10.6023/cjoc201308020 Previous Articles     Next Articles



方魏a, 刘国桂b, 黄晓飞b, 贾俊a, 王兴旺b   

  1. a. 苏州大学分析测试中心 苏州 215123;
    b. 苏州大学材料与化学化工学部 苏州 215123
  • 收稿日期:2013-08-16 修回日期:2013-12-18 发布日期:2014-02-12
  • 通讯作者: 贾俊
  • 基金资助:

    国家自然科学基金(No. 21272166)和江苏省属高校自然科学研究(No. 13KJA150004)资助项目.

Organic Base Catalyzed Cascade Phospho-Aldol-Brook Rearrangement Reaction of Isatins with H-phosphonates

Fang Weia, Liu Guoguib, Huang Xiaofeib, Jia Juna, Wang Xingwangb   

  1. a. Analysis and Testing Center, Soochow University, Suzhou 215123;
    b. College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123
  • Received:2013-08-16 Revised:2013-12-18 Published:2014-02-12
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21272166) and the Major Basic Research Project of the Natural Science Foundation of the Jiangsu Higher Education Institutions (No. 13KJA150004).

A cascade phospho-aldol-Brook rearrangement reaction of isatins with H-phosphonates was reported by the use of the organic base, such as 1,1,3,3-tetramethylguanidine (TMG) or 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), as an organocatalyst. Two series of 2-oxoindolin-3-yl phosphates were obtained in good to excellent yields under mild reaction conditions.

Key words: α-oxindole-phosphonates, isatins, H-phosphonates, Brook rearrangement, cascade reaction