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

[1] Recent progress in chiral Bronsted acid catalysis [J].

Akiyama, Takahiko ;

Itoh, Junji ;

Fuchibe, Kohei .

ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (09) :999-1010

[2]

[Anonymous], 2008, ANGEW CHEM

[3]

[Anonymous], 2009, ANGEW CHEM-GER EDIT

[4] Thiourea-Catalyzed Highly Enantio- and Diastereoselective Additions of Oxindoles to Nitroolefins: Application to the Formal Synthesis of (+)-Physostigmine [J].

Bui, Tommy ;

Syed, Salahuddin ;

Barbas, Carlos F., III .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (25) :8758-+

[5] Asymmetric catalysis with bifunctional cinchona alkaloid-based urea and thiourea organocatalysts [J].

Connon, Stephen J. .

CHEMICAL COMMUNICATIONS, 2008, (22) :2499-2510

[6] Organocatalysis mediated by (thio)urea derivatives [J].

Connon, Stephen J. .

CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (21) :5418-5427

[7] An asymmetric approach to coumarin anticoagulants via hetero-Diels-Alder cycloaddition [J].

Cravotto, G ;

Nano, GM ;

Palmisano, G ;

Tagliapietra, S .

TETRAHEDRON-ASYMMETRY, 2001, 12 (05) :707-709

[8]

Dickmeiss G., 2009, ANGEW CHEM, V121, P6778

[9] Organocatalytic Asymmetric Desymmetrization-Fragmentation of Cyclic Ketones [J].

Dickmeiss, Gustav ;

De Sio, Vincenzo ;

Udmark, Jonas ;

Poulsen, Thomas B. ;

Marcos, Vanesa ;

Jorgensen, Karl Anker .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (36) :6650-6653

[10] ARYLLEAD-MEDIATED SYNTHESIS OF LINEAR 3-ARYLPYRANOCOUMARINS - SYNTHESIS OF ROBUSTIN AND ROBUSTIC ACID [J].

DONNELLY, DMX ;

MOLLOY, DJ ;

REILLY, JP ;

FINET, JP .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (20) :2531-2534

← 1 2 3 4 5 6 7 →