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

页码：3164 / 3170

页数：7

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