Aryne-Induced Novel Tandem 1,2-Addition/(3+2) Cycloaddition to Generate Imidazolidines and Pyrrolidines

被引：60

作者：

Swain, Sharada P. ^{[1
,2
]}

Shih, Yi-Chun ^{[1
,2
]}

Tsay, Shwu-Chen ^{[1
,2
,3
]}

Jacob, Joby ^{[1
,2
]}

Lin, Chun-Cheng ^{[1
,2
]}

Hwang, Kuo Chu ^{[1
,2
]}

Horng, Jia-Cherng ^{[1
,2
]}

Hwu, Jih Ru ^{[1
,2
,3
]}

机构：

[1] Natl Tsing Hua Univ, Dept Chem, Hsinchu 30013, Taiwan

[2] Natl Tsing Hua Univ, Frontier Res Ctr Fundamental & Appl Sci Matters, Hsinchu 30013, Taiwan

[3] Natl Cent Univ, Dept Chem, Jhongli 32001, Taiwan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2015年 / 54卷 / 34期

关键词：

1,3-dipolar cycloaddition; arynes; azomethine ylides; imidazolidines; pyrrolidines; AZOMETHINE YLIDES; 1,3-DIPOLAR CYCLOADDITION; BENZYNE; RING; FRAGMENTATION; CHEMISTRY; INSERTION; STRATEGY; DIAMINES; ALKENES;

D O I：

10.1002/anie.201503319

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new "single-flask" method was developed for the synthesis of imidazolidines and pyrrolidines with high stereo-selectivity. First, a Schiff base was arylated with an aryne. Second, an intramolecular proton transfer took place from the methylene position to the anionic aryne ring. Third, the resultant ylide reacted with a second equivalent of the same Schiff base in situ or an electron-deficient alkene through a (3+2) cycloaddition. These sequential tandem 1,2-addition/(3+2) cycloaddition reactions led to the desired heterocycles in 63-88% yields.

引用

页码：9926 / 9930

页数：5

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