Diastereo- and enantioselective nitro-Mannich reaction of isatin-derived N-Boc ketimines catalyzed by chiral phase-transfer catalysts

被引：14

作者：

Liu, Yuxin ^{[1
]}

Wang, Jingdong ^{[1
]}

Wei, Zhonglin ^{[1
]}

Cao, Jungang ^{[1
]}

Liang, Dapeng ^{[1
]}

Lin, Yingjie ^{[1
]}

Duan, Haifeng ^{[1
]}

机构：

[1] Jilin Univ, Coll Chem, Dept Organ Chem, 2699 Qianjin St, Changchun 130012, Jilin, Peoples R China

来源：

NEW JOURNAL OF CHEMISTRY | 2018年 / 42卷 / 03期

基金：

中国国家自然科学基金;

关键词：

AZA-HENRY REACTION; CYCLIC TRIFLUOROMETHYL KETIMINES; HIGHLY EFFICIENT; ASYMMETRIC-SYNTHESIS; MICHAEL ADDITION; BIFUNCTIONAL ORGANOCATALYST; CINCHONA ALKALOIDS; BEARING; CONSTRUCTION; DERIVATIVES;

D O I：

10.1039/c7nj04527a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly diastereo- and enantioselective nitro-Mannich reaction of isatin-derived ketimines with alpha-aryl nitromethane catalyzed by Cinchona alkaloid-derived phase-transfer catalysts bearing multiple hydrogen-bonding donors (the first metal-free catalytic systems used in this reaction) was developed. A series of 3-substituted 3-amino-oxindoles were constructed using this protocol in excellent yields (96-99%) with high enantioselectivities (up to 95% ee) and diastereo-selectivities (up to 95:5 dr).

引用

收藏

页码：1608 / 1611

页数：4

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