Synthesis of Optically Active 2H-Thiopyrano[2,3-b]quinolines with Three Contiguous Stereocenters via an Organocatalytic Asymmetric Tandem Michael-Henry Reaction

被引：64

作者：

Wu, Lulu ^{[1
]}

Wang, Youming ^{[1
]}

Song, Haibin ^{[1
]}

Tang, Liangfu ^{[1
]}

Zhou, Zhenghong ^{[1
]}

Tang, Chuchi ^{[1
]}

机构：

[1] Nankai Univ, Inst Elementoorgan Chem, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2013年 / 355卷 / 06期

基金：

中国国家自然科学基金;

关键词：

Henry reaction; Michael addition; nitrooelfins; tandem reactions; 2H-thiopyrano[2; 3-b]quinolines; ALDOL REACTIONS; SUPPORTED SYNTHESIS; QUINOLINES; ANTAGONISTS; BINDING; SERIES;

D O I：

10.1002/adsc.201300086

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Optically active 2H-thiopyrano[2,3-b]quinolines with three contiguous stereocenters have been synthesized via a chiral bifunctional squaramide-catalyzed tandem MichaelHenry reaction between 2-mercaptoquinoline-3-carbaldehydes and nitroolefins. The reactions proceed with excellent diastereo- and enantioselectivity to give the title compounds in high yields with high levels of diastereo- and enantioselectivity (up to >99/1 dr and >99% ee, respectively).

引用

页码：1053 / 1057

页数：5

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