Chiral N,N′-Dioxide-Zinc(II) Complex-Catalyzed Asymmetric Aza-Friedel-Crafts Reaction of Isatin-Derived Ketimines with Indoles

被引：38
作者：
Zhang, Xiying [1 ]
Zhang, Jianlin [1 ]
Lin, Lili [1 ]
Zheng, Haifeng [1 ]
Wu, Wangbin [1 ]
Liu, Xiaohua [1 ]
Feng, Xiaoming [1 ]
机构：
[1] Sichuan Univ, Coll Chem, Minist Educ, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2016年 / 358卷 / 19期
基金：
中国国家自然科学基金;
关键词：
asymmetric catalysis; aza-Friedel-Crafts reaction; N; '-dioxides; isatin-derived ketimines; zinc(II); BAYLIS-HILLMAN REACTION; HIGHLY ENANTIOSELECTIVE ADDITION; MANNICH REACTION; 1,3-DIPOLAR CYCLOADDITIONS; AZOMETHINE YLIDE; HENRY REACTION; CONSTRUCTION; BEARING; ACCESS; IMINES;
D O I：
10.1002/adsc.201600630
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
A highly efficient chiral N,N'-dioxidezinc(II) complex catalytic system has been developed for the enantioselective aza-Friedel-Crafts reaction of isatin-derived ketimines with indoles. A series of enantiomerically enriched 3-indolyl-3-ami-nooxindoles containing a tetrasubstituted stereocenter were obtained in up to 99% yield with up to 96% ee. Furthermore, control experiments provide a fundamental sight into the mechanism of the reaction.
引用
收藏
页码：3021 / 3026
页数：6
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