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

doi:10.6023/cjoc201904041

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (8): 2235-2242.DOI: 10.6023/cjoc201904041 Previous Articles Next Articles

Special Issue: 陈茹玉先生诞辰100周年；元素有机化学合辑2018-2019

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膦催化水杨醛亚胺与马来酰亚胺的[4+1]环化反应及螺[苯并呋喃-2,3'-吡咯烷]衍生物的合成

杨梅^a, 曹仕轩^a, 贺峥杰^a,b

a 南开大学元素有机化学国家重点实验室天津 300071;
b 天津化学化工协同创新中心天津 300071

收稿日期:2019-04-16 修回日期:2019-05-07 发布日期:2019-05-15
通讯作者: 贺峥杰 E-mail:zhengjiehe@nankai.edu.cn
基金资助:
国家自然科学基金（Nos.21472096，21272119）资助项目.

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

Received:2019-04-16 Revised:2019-05-07 Published:2019-05-15
Contact: 10.6023/cjoc201904041 E-mail:zhengjiehe@nankai.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21472096, 21272119).

1. Phosphine-Catalyzed[4+1] Annulation of Salicyl Imines with Maleimides and Synthesis of Spiro[benzofuran-2,3'-pyrrolidine] Derivatives.PDF(783KB)

Abstract

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.

Key words: phosphine, [4+1]annulation reaction, imine, maleimide, synthesis

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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]. Chin. J. Org. Chem., 2019, 39(8): 2235-2242.

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膦催化水杨醛亚胺与马来酰亚胺的[4+1]环化反应及螺[苯并呋喃-2,3'-吡咯烷]衍生物的合成

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

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