A Three-Component Reaction Based on a Remote-Group-Directed Dynamic Kinetic Aza-Michael Addition: Stereoselective Synthesis of Imidazolidin-4-ones

被引：14

作者：

Xu, Zhenghu ^{[1
]}

Buechler, Tyler ^{[1
]}

Wheeler, Kraig ^{[2
]}

Wang, Hong ^{[1
]}

机构：

[1] Miami Univ, Dept Chem & Biochem, Oxford, OH 45056 USA

[2] Eastern Illinois Univ, Dept Chem, Charleston, IL 61920 USA

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2010年 / 16卷 / 10期

基金：

美国国家科学基金会;

关键词：

Bronsted acid catalysis; diastereoselectivity; dynamic kinetic alkylation; Michael addition; multicomponent reactions; ASYMMETRIC-SYNTHESIS; MULTICOMPONENT REACTIONS; BRONSTED ACID; AMINO-ACIDS; 1,3-DIPOLAR CYCLOADDITION; CONJUGATE ADDITION; ORGANIC CATALYSIS; DOMINO REACTIONS; CHIRAL GLYCINE; SULFINYL GROUP;

D O I：

10.1002/chem.200903508

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Figure Presented) In control: An α-amino amide reacted with an aldehyde and a Michael acceptor to form stable imidazolidin-4-ones with high stereoselectivity. A dynamic kinetic aza-Michael addition was discovered and applied to the three-component reaction to enforce high stereoselectivity. A remote group was incorporated to invert the reaction process and direct the reaction towards the desired product (see scheme). © 2010 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：2972 / 2976

页数：5

共 12 条

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