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

doi:10.6023/cjoc201308020

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

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有机碱催化的H-亚磷酸酯与靛红及其衍生物的phospho-Aldol-Brook重排串联反应

方魏^a, 刘国桂^b, 黄晓飞^b, 贾俊^a, 王兴旺^b

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 E-mail:jiajun@suda.edu.cn
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 Wei^a, Liu Guogui^b, Huang Xiaofei^b, Jia Jun^a, Wang Xingwang^b

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).

1. Organic Base Catalyzed Cascade Phospho-Aldol-Brook Rearrangement Reaction of Isatins with H-phosphonates.PDF(2015KB)

Abstract

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

Cite this article

Fang Wei, Liu Guogui, Huang Xiaofei, Jia Jun, Wang Xingwang. Organic Base Catalyzed Cascade Phospho-Aldol-Brook Rearrangement Reaction of Isatins with H-phosphonates[J]. Chin. J. Org. Chem., 2014, 34(6): 1177-1182.

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有机碱催化的H-亚磷酸酯与靛红及其衍生物的phospho-Aldol-Brook重排串联反应

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

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