Citation: Yang Mei, Cao Shixuan, He Zhengjie. Phosphine-Catalyzed[4+1] Annulation of Salicyl Imines with Maleimides and Synthesis of Spiro[benzofuran-2, 3'-pyrrolidine] Derivatives[J]. Chinese Journal of Organic Chemistry, ;2019, 39(8): 2235-2242. doi: 10.6023/cjoc201904041 shu

Phosphine-Catalyzed[4+1] Annulation of Salicyl Imines with Maleimides and Synthesis of Spiro[benzofuran-2, 3'-pyrrolidine] Derivatives

Yang Mei ^a ,
Cao Shixuan ^a ,
He Zhengjie ^a,b,,

a.
State Key Laboratory of Elemento-organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071
b.
Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300071

Corresponding author: He Zhengjie, zhengjiehe@nankai.edu.cn
Received Date: 16 April 2019
Revised Date: 7 May 2019
Available Online: 15 August 2019
Fund Project: the National Natural Science Foundation of China 21472096Project supported by the National Natural Science Foundation of China (Nos. 21472096, 21272119)the National Natural Science Foundation of China 21272119

Figures(4)

In this work, a phosphine-catalyzed[4+1] annulation between salicyl imines and maleimides has been successfully developed, which readily produces spiro[benzofuran-2, 3'-pyrrolidine] derivatives in 44%~99% yields. The annulation products were obtained as a pair of syn-and anti-isomers with dr 1.6:1~5:1. The syn-and anti-isomers can be readily separated by column chromatography on silica gel. Thus, this reaction constitutes a simple and efficient method for the synthesis of spiro[benzofuran-2, 3'-pyrrolidines]. Presumably, the reaction is initiated by in situ generated non-allylic P-ylide from maleimide and PPh₃, and proceeds through a cascade sequence of nucleophilic addition/intramolecular S_N2-like substitution. It accordingly represents a new example of the phosphine-catalyzed[4+1] annulation via in situ generated non-allylic P-ylides.
- phosphine,
- [4+1]annulation reaction,
- imine,
- maleimide,
- synthesis
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