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
收藏
页码：1482 / 1489
页数：8
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