Asymmetric Catalytic 1,3-Dipolar Cycloaddition Reaction of Nitrile Imines for the Synthesis of Chiral Spiro-Pyrazoline-Oxindoles

被引：119

作者：

Wang, Gang ^{[1
]}

Liu, Xiaohua ^{[1
]}

Huang, Tianyu ^{[1
]}

Kuang, Yulong ^{[1
]}

Lin, Lili ^{[1
]}

Feng, Xiaoming ^{[1
]}

机构：

[1] Sichuan Univ, Minist Educ, Coll Chem, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 01期

基金：

中国国家自然科学基金;

关键词：

HIGHLY ENANTIOSELECTIVE SYNTHESIS; AZOMETHINE IMINES; NITRONES; YLIDES; CONSTRUCTION; DIAZOESTERS; ISATINS; KETONES;

D O I：

10.1021/ol303097j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new 1,3-dipolar cycloaddition of nitrile imines with 3-alkenyl-oxindoles was catalyzed by a new chiral Mg(ClO4)(2) complex of an N,N'-dioxide ligand. The reaction is so far the sole catalytic synthesis of spiro-pyrazoline-oxindole derivatives. A wide variety of substrates were explored to obtain good yields (up to 98%) and excellent enantioselectivities (up to 99%). This cycloaddition expands the scope of propargyl anion type 1,3-dipole in the construction of 2-pyrazoline subunit.

引用

页码：76 / 79

页数：4

共 54 条

[21] Asymmetric 1,3-dipolar cycloadditions of acrylamides [J].

Kissane, Marie ;

Maguire, Anita R. .

CHEMICAL SOCIETY REVIEWS, 2010, 39 (02) :845-883

[22] A Catalytic Asymmetric Ring-Expansion Reaction of Isatins and a-Alkyl-a-Diazoesters: Highly Efficient Synthesis of Functionalized 2-Quinolone Derivatives [J].

Li, Wei ;

Liu, Xiaohua ;

Hao, Xiaoyu ;

Cai, Yunfei ;

Lin, Lili ;

Feng, Xiaoming .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (34) :8644-8647

[23] New Electrophilic Addition of α-Diazoesters with Ketones for Enantioselective C-N Bond Formation [J].

Li, Wei ;

Liu, Xiaohua ;

Hao, Xiaoyu ;

Hu, Xiaolei ;

Chu, Yangyang ;

Cao, Weidi ;

Qin, Song ;

Hu, Changwei ;

Lin, Lili ;

Feng, Xiaoming .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (39) :15268-15271

[24]

Liu, 2011, Scandium: Compounds, Productions, and Applications, P1

[25] Catalytic asymmetric 1,3-dipolar cycloaddition of N-unprotected 2-oxoindolin-3-ylidene derivatives and azomethine ylides for the construction of spirooxindole-pyrrolidines [J].

Liu, Tang-Lin ;

Xue, Zhi-Yong ;

Tao, Hai-Yan ;

Wang, Chun-Jiang .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (06) :1980-1986

[26] Chiral N,N′-Dioxides: New Ligands and Organocatalysts for Catalytic Asymmetric Reactions [J].

Liu, Xiaohua ;

Lin, Lili ;

Feng, Xiaoming .

ACCOUNTS OF CHEMICAL RESEARCH, 2011, 44 (08) :574-587

[27]

Lopez-Perez A., 2009, ANGEW CHEM, V121, P346

[28] The Phenylsulfonyl Group as a Temporal Regiochemical Controller in the Catalytic Asymmetric 1,3-Dipolar Cycloaddition of Azomethine Ylides [J].

Lopez-Perez, Ana ;

Adrio, Javier ;

Carretero, Juan C. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (02) :340-343

[29]

Mogilaiah K, 1998, INDIAN J CHEM B, V37, P139

[30] Stereoselective cycloadditions of nitrilimines as a source of enantiopure heterocycles [J].

Molteni, G .

HETEROCYCLES, 2005, 65 (10) :2513-2537

← 1 2 3 4 5 6 →