A highly enantioselective catalytic domino aza-Michael/aldol reaction:: One-pot organocatalytic asymmetric synthesis of 1,2-dihydroquinolidines

被引：111

作者：

Sunden, Henrik

Rios, Ramon

Ibrahem, Ismail

Zhao, Gui-Ling

Eriksson, Lars

Cordova, Armando ^{[1
]}

机构：

[1] Univ Stockholm, Arrhenius Lab, Dept Organ Chem, S-10691 Stockholm, Sweden

[2] Univ Stockholm, Arrhenius Lab, Dept Struct Chem, S-10691 Stockholm, Sweden

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2007年 / 349卷 / 06期

关键词：

asymmetric catalysis; aza-Michael reaction; domino reactions; nitrogen heterocycles; alpha; beta-unsaturated aldehydes;

D O I：

10.1002/adsc.200600513

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The highly enantioselective organocatalytic domino aza-Michael/aldol reaction is presented. The unprecedented, chiral amine-catalyzed asymmetric domino reactions between 2-aminobenzaldehydes and a,(3-unsaturated aldehydes proceed with excellent chemo- and enantioselectivity to give the corresponding pharmaceutically valuable 1,2-dihydroquinolines derivatives in high yields with 90 to > 99 % ee.

引用

页码：827 / 832

页数：6

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[1] NOVEL, POTENT, AND SELECTIVE 5-HT3 RECEPTOR ANTAGONISTS BASED ON THE ARYLPIPERAZINE SKELETON - SYNTHESIS, STRUCTURE, BIOLOGICAL-ACTIVITY, AND COMPARATIVE MOLECULAR-FIELD ANALYSIS STUDIES [J].