Dual Organocatalytic Ion-Pair Assemblies: A Highly Efficient Approach for the Enantioselective Oxa-Michael-Mannich Reaction of Salicylic Aldehydes with Cyclohexenones

被引：57

作者：

Xia, Ai-Bao ^{[1
]}

Xu, Dan-Qian ^{[1
]}

Luo, Shu-Ping ^{[1
]}

Jiang, Jun-Rong ^{[1
]}

Tang, Jie ^{[1
]}

Wang, Yi-Feng ^{[1
]}

Xu, Zhen-Yuan ^{[1
]}

机构：

[1] Zhejiang Univ Technol, State Key Lab Breeding Base Green Chem Synth Tech, Hangzhou, Zhejiang, Peoples R China

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2010年 / 16卷 / 03期

基金：

中国国家自然科学基金;

关键词：

asymmetric synthesis; dual activation; organocatalysis; oxa-Michael-Mannich reaction; self-assembly; CATALYTIC ASYMMETRIC-SYNTHESIS; INTERMOLECULAR ALDOL REACTIONS; AMINO-ACIDS; ELECTROSPRAY-IONIZATION; MASS-SPECTROMETRY; ALPHA; BETA-UNSATURATED KETONES; CERCOSPORA-BETICOLA; ADDITION-REACTIONS; TETRAHYDROXANTHENONES; COMBINATORIAL;

D O I：

10.1002/chem.200902540

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A study was conducted to demonstrate a novel type of bifunctional catalyst generated by the self-assembly of pyrrolidines and readily available primary amino acids. It was demonstrated that the protonation of the aromatic nitrogen atom of pyrrolidines by amino acids spontaneously led to ion-pair assemblies. The self-assembled catalysts possessed dual activation centers and enabled the catalysis of the electrophilic and nucleophilic substrates similar to catalysis by enzymes. The simultaneous activation of cyclohex-2-enone and salicylic aldehyde by pyrrolidines and amino acids generated the transient ion pairs through iminiums and imines. The resultant assemblies ensured that the enantioselective domino oxa-Michael addition and intramolecular Mannich reaction proceeded to afford the corresponding products upon hydrolysis.

引用

页码：801 / 804

页数：4

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