Asymmetric Catalytic Synthesis of Hexahydropyrrolo-isoquinolines via Three-Component 1,3-Dipolar-Cycloaddition

被引：14
|
作者：
Li, Zhaojing [1 ]
Xu, Nian [1 ]
Guo, Ning [1 ]
Zhou, Yuqiao [1 ]
Lin, Lili [1 ]
Feng, Xiaoming [1 ]
机构：
[1] Sichuan Univ, Coll Chem, Key Lab Green Chem & Technol, Minist Educ, Chengdu, Peoples R China
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2021年 / 27卷 / 60期
关键词：
3+2]-cycloaddition; asymmetric catalysis; N; N'-dioxides; pyrrolo[2; 1-a]isoquinoline; yttrium; 1,3-DIPOLAR CYCLOADDITION; N-YLIDES; ENANTIOSELECTIVE SYNTHESIS; REGIOSELECTIVE SYNTHESIS; CASCADE; AMIDES; LAMELLARINS; DERIVATIVES; ALKALOIDS; BODIPY;
D O I：
10.1002/chem.202102476
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An asymmetric three-component 1,3-dipolar cycloaddition of 3,4-dihydroisoquinolines, bromoacetates and alpha,beta-unsaturated pyrazole amide is realized by using a chiral N,N'-dioxide-Y(OTf)(3) complex as the catalyst. The process includes a base-promoted formation of dihydroisoquinolium ylides in situ, and a chiral Lewis acid-catalyzed asymmetric [3+2] cycloaddition with alpha,beta-unsaturated pyrazole amides. A series of hexahydropyrrolo-isoquinolines are obtained in moderate to good yields with excellent diastereo- and enantioselectivities.
引用
收藏
页码：14841 / 14845
页数：5
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