Metal Catalysis versus Organocatalysis in the Catalytic Asymmetric Synthesis of 3-Hydroxyoxindole

被引：29

作者：

Liu, Yunlin ^{[1
]}

Zhu, Feng ^{[1
]}

Wang, Cuihong ^{[1
]}

Zhou, Jian ^{[1
]}

机构：

[1] E China Normal Univ, Dept Chem, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China

来源：

CHINESE JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 33卷 / 08期

基金：

中国国家自然科学基金;

关键词：

3-substituted-3-hydroxyoxindole; asymmetric catalysis; metal catalysis; organocatalysis; BAYLIS-HILLMAN REACTION; HIGHLY ENANTIOSELECTIVE SYNTHESIS; FRIEDEL-CRAFTS REACTION; ALDOL REACTION; ARYLBORONIC ACIDS; STEREOSELECTIVE-SYNTHESIS; UNACTIVATED KETONES; SUBSTITUTED ISATINS; QUATERNARY CARBON; CONVOLUTAMYDINE E;

D O I：

10.6023/cjoc201303038

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

3-Substituted 3-hydroxyoxindoles are widely encountered in a large number of natural products, drugs and pharmaceutically active compounds. The catalytic asymmetric construction of this privileged skeleton has attracted great attention from synthetic chemistry, and much progress has been made in recent years. This review summarizes the advances in the catalytic enantioselective synthesis of four important types of subunits of 3-substituted 3-hydroxyoxindoles, and focuses on the discussion of the differences and advantages of metal catalysis and organocatalysis.

引用

页码：1595 / 1615

页数：21

共 122 条

[21] Rh(I)-Catalyzed Asymmetric 1,2-Addition to α-Diketones with Chiral Sulfur-Alkene Hybrid Ligands
Feng, Xiangqing
Hie, Yanzhao
Yang, Jing
Du, Haifeng
[J]. ORGANIC LETTERS, 2012, 14 (02) : 624 - 627
[22] Pyrrolidinyl-spirooxindole natural products as inspirations for the development of potential therapeutic agents
Galliford, Chris V.
Scheidt, Karl A.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (46) : 8748 - 8758
[23] Recent Progress in Lewis Base Activation and Control of Stereoselectivity in the Additions of Trimethylsilyl Nucleophiles
Gawronski, Jacek
Wascinska, Natalia
Gajewy, Jadwiga
[J]. CHEMICAL REVIEWS, 2008, 108 (12) : 5227 - 5252
[24] Construction of Chiral Quaternary Carbon through Morita-Baylis-Hillman Reaction: An Enantioselective Approach to 3-Substituted 3-Hydroxyoxindole Derivatives
Guan, Xiao-Yang
Wei, Yin
Shi, Min
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (46) : 13617 - 13621
[25] Rh(I)-catalyzed asymmetric addition of arylboronic acids to NH isatins
Gui, Jiangyang
Chen, Guihua
Cao, Peng
Liao, Jian
[J]. TETRAHEDRON-ASYMMETRY, 2012, 23 (08) : 554 - 563
[26] Quinidine Thiourea-Catalyzed Aldol Reaction of Unactivated Ketones: Highly Enantioselective Synthesis of 3-Alkyl-3-hydroxy-indolin-2-ones
Guo, Qunsheng
Bhanushali, Mayur
Zhao, Cong-Gui
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (49) : 9460 - 9464
[27] Enantioselective and Regioselective Indium(III)-Catalyzed Addition of Pyrroles to Isatins
Gutierrez, Elisa G.
Wong, Casey J.
Sahin, Aziza H.
Franz, Annaliese K.
[J]. ORGANIC LETTERS, 2011, 13 (21) : 5754 - 5757
[28] Scandium(III)-Catalyzed Enantioselective Allylation of Isatins Using Allylsilanes
Hanhan, Nadine V.
Tang, Yng C.
Tran, Ngon T.
Franz, Annaliese K.
[J]. ORGANIC LETTERS, 2012, 14 (09) : 2218 - 2221
[29] Catalytic Asymmetric Synthesis of Substituted 3-Hydroxy-2-Oxindoles
Hanhan, Nadine V.
Sahin, Aziza H.
Chang, Toby W.
Fettinger, James C.
Franz, Annaliese K.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (04) : 744 - 747
[30] Organocatalytic Enantioselective Decarboxylative Addition of Malonic Acids Half Thioesters to Isatins
Hara, Noriyuki
Nakamura, Shuichi
Funahashi, Yasuhiro
Shibata, Norio
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (16) : 2976 - 2980

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