Highly efficient asymmetric organocatalytic Friedel-Crafts alkylation of indoles with α,β-unsaturated aldehydes

被引：20

作者：

Jin, Shangbin ^{[1
]}

Li, Chenguang ^{[1
]}

Ma, Yuanhui ^{[1
]}

Kan, Yuhe ^{[2
]}

Zhang, Yong Jian ^{[1
]}

Zhang, Wanbin ^{[1
]}

机构：

[1] Shanghai Jiao Tong Univ, Sch Chem & Chem Engn, Shanghai 200240, Peoples R China

[2] Huaiyin Normal Univ, Sch Chem & Chem Engn, Huaian 223300, Jiangshu, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2010年 / 8卷 / 17期

基金：

中国国家自然科学基金;

关键词：

DIELS-ALDER REACTIONS; MICHAEL ADDITION; C-2-SYMMETRIC BIPYRROLIDINES; ENANTIOSELECTIVE SYNTHESIS; CATALYSIS; KETONES; AMINE;

D O I：

10.1039/c0ob00016g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The development of an improved organocatalyst, N-isopropylated bipyrrolidine 2a, for the asymmetric Friedel-Crafts alkylation of indoles with alpha,beta-unsaturated aldehydes has been presented. The new organocatalyst readily facilitates the enantioselective alkylation reaction, providing 3-alkylated indoles in good to high yields (62-89%) with high levels of enantioselectivity (80-93% ee) using only 2 mol% of catalyst loading.

引用

页码：4011 / 4015

页数：5

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