Enantioselective construction of 2,5-dihydropyrrole skeleton with quaternary stereogenic center via catalytic asymmetric 1,3-dipolar cycloaddition involving α-arylglycine esters

被引：49

作者：

Shi, Feng ^{[1
]}

Xing, Gui-Juan ^{[1
]}

Tan, Wei ^{[1
]}

Zhu, Ren-Yi ^{[1
]}

Tu, Shujiang ^{[1
]}

机构：

[1] Jiangsu Normal Univ, Sch Chem & Chem Engn, Xuzhou 221116, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2013年 / 11卷 / 09期

基金：

中国国家自然科学基金;

关键词：

CHIRAL BRONSTED ACID; MANNICH-TYPE REACTION; AZOMETHINE YLIDES; PROLINE DERIVATIVES; ONE-POT; NITROALKENES; CYCLIZATION; ALDEHYDES; IMINES;

D O I：

10.1039/c2ob26566d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A catalytic asymmetric construction of synthetically and biologically important 2,5-dihydropyrrole scaffolds with concomitant creation of multiple chiral carbon centers including one quaternary stereogenic center in high yields (up to 99%) and excellent enantioselectivities (up to 99% ee) has been established via an organocatalytic 1,3-dipolar cycloaddition using alpha-arylglycine esters as azomethine precursors. Moreover, a detailed investigation has been performed on the catalytic asymmetric 1,3-dipolar cycloadditions of alpha-arylglycine ester-generated azomethine ylides with alkynes, providing an efficient way to simultaneously access both 2,5-dihydropyrrole diastereomers in good enantioselectivities.

引用

页码：1482 / 1489

页数：8

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