Asymmetric tandem Michael addition/oxidation of pyrazolones with p-benzoquinone catalyzed by cinchona alkaloids

被引：19

作者：

He, Yuli ^{[1
]}

Bao, Xiaoze ^{[1
]}

Qu, Jingping ^{[1
]}

Wang, Baomin ^{[1
]}

机构：

[1] Dalian Univ Technol, Sch Pharmaceut Sci & Technol, State Key Lab Fine Chem, Dalian 116024, Peoples R China

来源：

TETRAHEDRON-ASYMMETRY | 2015年 / 26卷 / 23期

基金：

中国国家自然科学基金;

关键词：

ALPHA-ARYLATION; CONJUGATE ADDITION; DERIVATIVES; PYRAZOLIN-5-ONES; PYRAZOL-5-ONES; COMPLEXES; OXINDOLES; MALONATE; ACCESS; ESTERS;

D O I：

10.1016/j.tetasy.2015.10.006

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

By employing a natural cinchona alkaloid as a catalyst, the enantioselective tandem Michael addition/oxidation of 4-substituted pyrazol-5-ones with p-benzoquinones was realized. The reaction afforded a wide range of 4,4-disubstituted pyrazol-5-ones with moderate to good yields (up to 72%) and moderate to good enantioselectivities (up to 99%). (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：1382 / 1387

页数：6

共 43 条

[1]

Alba A.-N. R., 2011, EUR J ORG CHEM, V13, P18

[2] 1,4-Naphthoquinones in H-Bond-Directed Trienamine-Mediated Strategies [J].

Albrecht, Lukasz ;

Gomez, Clarisa Villegas ;

Jacobsen, Christian Borch ;

Jorgensen, Karl Anker .

ORGANIC LETTERS, 2013, 15 (12) :3010-3013

[3] Organocatalytic asymmetric vinylogous addition to quinones -: formation of optically active α-aryl ketones [J].

Aleman, Jose ;

Jacobsen, Christian Borch ;

Frisch, Kim ;

Overgaard, Jacob ;

Jorgensen, Karl Anker .

CHEMICAL COMMUNICATIONS, 2008, (05) :632-634

[4] Asymmetric organocatalytic α-arylation of aldehydes [J].

Aleman, Jose ;

Cabrera, Silvia ;

Maerten, Eddy ;

Overgaard, Jacob ;

Jorgensen, Karl Anker .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (29) :5520-5523

[5] Organocatalytic highly enantioselective α-arylation of β-ketoesters [J].

Aleman, Jose ;

Richter, Bo ;

Jorgensen, Karl Anker .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (29) :5515-5519

[6] Squaramides: Bridging from Molecular Recognition to Bifunctional Organocatalysis [J].

Aleman, Jose ;

Parra, Alejandro ;

Jiang, Hao ;

Jorgensen, Karl Anker .

CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (25) :6890-6899

[7] Synthesis and antimicrobial activity of some new heterocycles incorporating antipyrine moiety [J].

Bondock, Samir ;

Rabie, Ramy ;

Etman, Hassan A. ;

Fadda, Ahmed A. .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2008, 43 (10) :2122-2129

[8] PYRAZOLONE DERIVATIVES [J].

BROGDEN, RN .

DRUGS, 1986, 32 :60-70

[9] New Pd(II) and Pt(II) complexes with N,S-chelated pyrazolonate ligands:: Molecular and supramolecular structure and preliminary study of their in vitro antitumoral activity [J].

Casas, Jose S. ;

Castellano, Eduardo E. ;

Ellena, Javier ;

Garcia-Tasende, Maria S. ;

Perez-Paralle, M. Luz ;

Sanchez, Agustin ;

Sanchez-Gonzalez, Angeles ;

Sordo, Jos ;

Touceda, Angeles .

JOURNAL OF INORGANIC BIOCHEMISTRY, 2008, 102 (01) :33-45

[10] Highly Diastereoselective Synthesis of Spiropyrazolones [J].

Ceban, Victor ;

Olomola, Temitope O. ;

Meazza, Marta ;

Rios, Ramon .

MOLECULES, 2015, 20 (05) :8574-8582

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