Substrate-Controlled Regioselectivity Switch in a Three-Component 1,3-Dipolar Cycloaddition Reaction to Access 3,3′-Pyrrolidinyl-Spirooxindoles Derivatives

被引：14

作者：

Wang, Kai-Kai ^{[1
,2
]}

Li, Yan-Li ^{[3
]}

Chen, Rong-Xiang ^{[1
]}

Sun, Ai-Li ^{[2
]}

Wang, Zhan-Yong ^{[1
]}

Zhao, Ying-Chao ^{[1
]}

Wang, Ming-Yue ^{[1
]}

Sheng, Shi ^{[1
]}

机构：

[1] Xinxiang Univ, Sch Pharm, Xinxiang 453000, Henan, Peoples R China

[2] Key Lab Nanocarbon Modified Film Technol Engn Hen, Xinxiang 453000, Henan, Peoples R China

[3] Xinxiang Univ, Med Coll, Xinxiang 453000, Henan, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2022年 / 364卷 / 12期

基金：

中国国家自然科学基金;

关键词：

1; 3-dipolar cycloaddition; spirooxindoles; three-component reaction; azomethine ylides; switchable; AZOMETHINE YLIDES; STEREOSELECTIVE-SYNTHESIS; MULTICOMPONENT REACTIONS; SPIROOXINDOLES; DIVERSITY; RHYNCHOPHYLLINE; CONSTRUCTION; OXINDOLES; DESIGN;

D O I：

10.1002/adsc.202200269

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The additive-free 1,3-dipolar cycloaddition reaction of isatin-derived azomethine ylides with alpha-cyano-alpha,beta-unsaturated compounds was developed, which enabled diversity-oriented synthesis of a series of novel and structurally complex 3,3 '-pyrrolidinyl-spirooxindoles derivatives containing four contiguous and two quaternary stereogenic centers in high yields (up to 92%) and excellent diastereoselectivities (up to >25:1 dr). The reaction displays switchable regioselectivity depending on the steric effect of the substrates.

引用

页码：2047 / 2052

页数：6

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