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

被引：28

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

页码：2204 / 2210

页数：7

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