Citation: Wu Ping, Gao Hong, Sun Jing, Yan Chao-Guo. 1, 3-Dipolar cycloaddition reaction for diastereoselective synthesis of functionalized dihydrospiro[indoline-3, 2'-pyrroles][J]. Chinese Chemical Letters, ;2017, 28(2): 329-332. doi: 10.1016/j.cclet.2016.07.016 shu

1, 3-Dipolar cycloaddition reaction for diastereoselective synthesis of functionalized dihydrospiro[indoline-3, 2'-pyrroles]

Wu Ping ^a ,
Gao Hong ^b ,
Sun Jing ^b ,
Yan Chao-Guo ^b,,

a.
Department of Biochemical Engineering, Yangzhou Polytechnic University, Yangzhou 225000, China
b.
College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou 225002, China

Corresponding author: Yan Chao-Guo, cgyan@yzu.edu.cn
Received Date: 12 May 2016
Revised Date: 22 June 2016
Accepted Date: 7 July 2016
Available Online: 18 February 2016

Figures(2)

The BF₃OEt₂ catalyzed one-pot 1, 3-dipolar cycloaddition reaction of benzylamines, isatins and dimethyl acetylenedicarboxylate in dry methylene dichloride afforded the functionalized dihydrospiro[indoline-3, 2'-pyrroles] in moderate to good yields and with high diastereoselectivity. The reaction was accomplished by the tandem 1, 3-dioplar cycloaddition of in situ generated azomethine ylide with acetylenedicarboxylate and the nucleophilic addition of pyrrole ring to second molecular acetylenedicarboxylate.
- One-pot reaction,
- 1, 3-Dipolar cycloaddition,
- Azomethine ylide,
- Electron-deficient alkyne,
- Spiro[indoline-3, 2'-pyrrole]
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