Chiral Squaramides as Highly Enantioselective Catalysts for Michael Addition Reactions of 4-Hydroxycoumarins and 4-Hydroxypyrone to β,γ-Unsaturated α-Keto Esters

被引：134

作者：

Xu, Dan-Qian ^{[1
]}

Wang, Yi-Feng ^{[1
]}

Zhang, Wei ^{[1
]}

Luo, Shu-Ping ^{[1
]}

Zhong, Ai-Guo ^{[2
]}

Xia, Ai-Bao ^{[1
]}

Xu, Zhen-Yuan ^{[1
]}

机构：

[1] Zhejiang Univ Technol, State Key Lab Breeding Base Green Chem Synth Tech, Hangzhou 310014, Zhejiang, Peoples R China

[2] Taizhou Coll, Dept Pharmaceut & Chem Engn, Linhai 317000, Zhejiang, Peoples R China

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2010年 / 16卷 / 14期

基金：

中国国家自然科学基金;

关键词：

asymmetric catalysis; hydrogen bonds; Michael addition; organocatalysis; squaramides; CYCLIC 1,3-DICARBONYL COMPOUNDS; ANTI-AIDS AGENTS; ASYMMETRIC CATALYSIS; DERIVATIVES; COMPLEXES; COUMARINS; CASCADE;

D O I：

10.1002/chem.201000094

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Figure Presented) Distance brings forth beauty: The first highly enantioselective organocatalytic Michael addition of 4-hydroxycoumarins and the analogous 4-hydroxy-6methyl-2-pyrone to β,γ-unsaturated α-keto esters by using chiral squaramides as the organocatalysts is disclosed. The efficiency of the process is attributed to the hydrogen-bonding activation (see scheme). © 2010 Wiley-VCH Verlag GmbH & Co. KGaA,.

引用

页码：4177 / 4180

页数：4

共 61 条

[31] Reactions of Cationic Gold(I) with Allenoates: Synthesis of Stable Organogold(I) Complexes and Mechanistic Investigations on Gold-Catalyzed Cyclizations [J].