Enantioselective Organocatalytic Domino Michael/Aldol Reactions: An Efficient Procedure for the Stereocontrolled Construction of 2H-Thiopyrano[2,3-b]quinoline Scaffolds

被引：27
|
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 & State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China
来源：
CHEMISTRY-AN ASIAN JOURNAL | 2013年 / 8卷 / 09期
基金：
中国国家自然科学基金;
关键词：
aldol reaction; enals; heterocycles; Michael addition; organocatalysis; ONE-POT SYNTHESIS; 3 CONTIGUOUS STEREOCENTERS; SOLVENT-FREE CONDITIONS; ALDOL REACTIONS; SUPPORTED SYNTHESIS; HENRY REACTION; DNA-BINDING; QUINOLINES; DERIVATIVES; TETRAHYDROTHIOPHENES;
D O I：
10.1002/asia.201300450
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An efficient procedure for the stereocontrolled construction of 2H-thiopyrano[2,3-b]quinoline scaffolds has been developed, starting from simple compounds. The domino Michael/aldol reactions between 2-mercaptobenzaldehydes and enals, promoted by chiral diphenylprolinol TMS ether, proceed with excellent chemo- and enantioselectivity to give the corresponding synthetically useful and pharmaceutically valuable 2H-thiopyrano[2,3-b]quinolines in high yields with 90-99% ee.
引用
收藏
页码：2204 / 2210
页数：7
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