Catalytic Asymmetric Construction of Quaternary -Amino Acid Containing Pyrrolidines through 1,3-Dipolar Cycloaddition of Azomethine Ylides to -Aminoacrylates

被引：47
|
作者：
Wang, Zheng [1 ,2 ]
Luo, Shuai [1 ,2 ]
Zhang, Shoude [1 ,2 ]
Yang, Wu-Lin [1 ,2 ]
Liu, Yang-Zi [1 ,2 ]
Li, Honglin [1 ,2 ]
Luo, Xiaoyan [1 ,2 ]
Deng, Wei-Ping [1 ,2 ]
机构：
[1] E China Univ Sci & Technol, Shanghai Key Lab New Drug Design, Shanghai 200237, Peoples R China
[2] E China Univ Sci & Technol, Sch Pharm, Shanghai 200237, Peoples R China
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2013年 / 19卷 / 21期
基金：
中国国家自然科学基金;
关键词：
-amino acids; asymmetric catalysis; azomethine ylides; cycloaddition; silver; ELECTRONIC CIRCULAR-DICHROISM; METABOTROPIC GLUTAMATE RECEPTORS; SELECTIVE 3+2 CYCLOADDITION; PROLINE DERIVATIVES; ENAMINE CATALYSIS; ORGANIC-COMPOUNDS; OPTICAL-ROTATION; NATURAL-PRODUCTS; COMPLEXES; LIGANDS;
D O I：
10.1002/chem.201300204
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The first catalytic enantioselective 1,3-dipolar cycloaddition of azomethine ylides to -aminoacrylate catalyzed by a AgOAc/ferrocenyl oxazolinylphosphine (FOXAP) system was developed, which exhibits excellent exo- and enantioselectivity (9299%ee). This process provides efficient access to useful 4-aminopyrrolidine-2,4-dicarboxylic acid (APDC)-like compounds containing a unique quaternary -amino acid unit.
引用
收藏
页码：6739 / 6745
页数：7
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