Chiral Squaramide-Catalyzed Asymmetric Mannich Reactions for Synthesis of Fluorinated 3,3-Bisoxindoles

被引：30
|
作者：
Li, Bing-Yu [1 ]
Du, Da-Ming [1 ]
机构：
[1] Beijing Inst Technol, Sch Chem & Chem Engn, 5 South Zhongguancun St, Beijing 100081, Peoples R China
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2018年 / 360卷 / 16期
基金：
中国国家自然科学基金;
关键词：
Asymmetric catalysis; Mannich addition; Organocatalysis; Bisoxindoles; Squaramides; ENANTIOSELECTIVE CONJUGATE ADDITION; 3,3-DISUBSTITUTED OXINDOLES; MEDICINAL CHEMISTRY; EFFICIENT ACCESS; VINYL SULFONE; CONSTRUCTION; ACIDS; 3-FLUOROOXINDOLES; 3-HALOOXINDOLES; REACTIVITY;
D O I：
10.1002/adsc.201800513
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
A squaramide-catalyzed asymmetric Mannich reaction of 3-fluorooxindoles to isatin-derived imines for synthesis of fluorinated 3,3-bisoxindoles with two contiguous stereocenters under mild conditions was developed. The corresponding 3,3-bisoxindoles were obtained in excellent yields with excellent diastereo- and enantioselectivities (up to 99% yield, >99:1dr and >99% ee). What's more, this reaction can be gram-scaled without compromising yield and stereoselectivity.
引用
收藏
页码：3164 / 3170
页数：7
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