Synthesis of N-Alkoxycarbonyl Ketimines Derived from Isatins and Their Application in Enantioselective Synthesis of 3-Aminooxindoles

被引：171

作者：

Yan, Wenjin

Wang, Dong

Feng, Jingchao

Li, Peng

Zhao, Depeng

Wang, Rui ^{[1
]}

机构：

[1] Lanzhou Univ, Key Lab Preclin Study New Drugs Gansu Prov, Sch Basic Med Sci, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 10期

基金：

中国国家自然科学基金;

关键词：

ORGANOCATALYTIC ALPHA-AMINATION; CATALYTIC ASYMMETRIC-SYNTHESIS; OXINDOLES; IMINES; DERIVATIVES; FACILE; POTENT;

D O I：

10.1021/ol3007953

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple and general method in the synthesis of N-alkoxycarbonyl ketimines derived from isatins has been described first. Generally, the enantioselective addition of 1,3-dicarbonyl compounds to this kind of ketimine affords chiral 3-amino oxindoles in high yield and excellent ee.

引用

页码：2512 / 2515

页数：4

共 41 条

[1] Highly Enantioselective Organocatalytic α-Amination Reactions of Aryl Oxindoles: Developing Designer Multifunctional Alkaloid Catalysts [J].

Bui, Tommy ;

Hernandez-Torres, Gloria ;

Milite, Ciro ;

Barbas, Carlos F., III .

ORGANIC LETTERS, 2010, 12 (24) :5696-5699

[2] Expanding the Scope of Cinchona Alkaloid-Catalyzed Enantioselective α-Aminations of Oxindoles: A Versatile Approach to Optically Active 3-Amino-2-oxindole Derivatives [J].

Bui, Tommy ;

Borregan, Mar ;

Barbas, Carlos F., III .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (23) :8935-8938

[3] Enantioselective Michael/Cyclization Reaction Sequence: Scaffold-Inspired Synthesis of Spirooxindoles with Multiple Stereocenters [J].

Cao, Yiming ;

Jiang, Xianxing ;

Liu, Luping ;

Shen, Fangfang ;

Zhang, Futing ;

Wang, Rui .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (39) :9124-9127

[4] Highly Enantioselective and Organocatalytic α-Amination of 2-Oxindoles [J].

Cheng, Liang ;

Liu, Li ;

Wang, Dong ;

Chen, Yong-Jun .

ORGANIC LETTERS, 2009, 11 (17) :3874-3877

[5] The asymmetric intramolecular Heck reaction in natural product total synthesis [J].

Dounay, AB ;

Overman, LE .

CHEMICAL REVIEWS, 2003, 103 (08) :2945-2963

[6] Pyrrolidinyl-spirooxindole natural products as inspirations for the development of potential therapeutic agents [J].

Galliford, Chris V. ;

Scheidt, Karl A. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (46) :8748-8758

[7] Enantioselective and Solvent-Controlled Diastereoselective Mannich Reaction of Isatin Imines with Hydroxyacetone: Synthesis of 3-Substituted 3-Aminooxindoles [J].

Guo, Qi-Xiang ;

Liu, Yu-Wan ;

Li, Xing-Cheng ;

Zhong, Ling-Zhi ;

Peng, Yun-Gui .

JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (07) :3589-3594

[8] Development of a Practical Synthetic Method for N-tert-Butoxycarbonyl α-Ketimino Esters [J].

Hashimoto, Takuya ;

Yamamoto, Kumiko ;

Maruoka, Keiji .

CHEMISTRY LETTERS, 2011, 40 (03) :326-327

[9] Enantioselective Michael addition to α,β-unsaturated imides catalyzed by a bifunctional organocatalyst [J].

Hoashi, Y ;

Okino, T ;

Takemoto, Y .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (26) :4032-4035

[10]

Jiang X., 2012, ADV SYNTH CATAL, DOI [10.1002/adsc.201100796, DOI 10.1002/ADSC.201100796]

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