The asymmetric synthesis of CF3-containing spiro[pyrrolidin-3,2′-oxindole] through the organocatalytic 1,3-dipolar cycloaddition reaction

被引：137

作者：

Ma, Mingxia ^{[1
]}

Zhu, Yuanyuan ^{[1
]}

Sun, Quantao ^{[1
]}

Li, Xiaoyuan ^{[1
]}

Su, Jinhuan ^{[1
]}

Zhao, Long ^{[1
]}

Zhao, Yanyan ^{[1
]}

Qiu, Shuai ^{[1
]}

Yan, Wenjin ^{[1
]}

Wang, Kairong ^{[1
]}

Wang, Rui ^{[1
,2
]}

机构：

[1] Lanzhou Univ, Sch Basic Med Sci, Dept Pharmacol, Key Lab Preclin Study New Drugs Gansu Prov, Lanzhou 730000, Peoples R China

[2] Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2015年 / 51卷 / 42期

基金：

中国国家自然科学基金;

关键词：

HIGHLY ENANTIOSELECTIVE ADDITION; DIVERSITY-ORIENTED SYNTHESIS; AZOMETHINE YLIDES; DIASTEREOSELECTIVE SYNTHESIS; OXINDOLES; ALKYNES; DERIVATIVES; KETIMINES; CONSTRUCTION; EFFICIENT;

D O I：

10.1039/c4cc10216a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new strategy for the construction of optically active 5 '-CF3 spiro[pyrrolidin-3,2 '-oxindole] was described. A series of unprecedented 1,3-dipoles were obtained by condensation of CF3CH2NH2 with isatins. The 1,3-dipolar cycloaddition reactions of these ketimines with enals gave the products bearing four contiguous stereogenic centers in excellent yields, diastereoselectivities and enantioselectivities.

引用

页码：8789 / 8792

页数：4

共 66 条

[1] Recent advances in the catalytic asymmetric 1,3-dipolar cycloaddition of azomethine ylides [J].

Adrio, Javier ;

Carretero, Juan C. .

CHEMICAL COMMUNICATIONS, 2014, 50 (83) :12434-12446

[2] Novel dipolarophiles and dipoles in the metal-catalyzed enantioselective 1,3-dipolar cycloaddition of azomethine ylides [J].

Adrio, Javier ;

Carretero, Juan C. .

CHEMICAL COMMUNICATIONS, 2011, 47 (24) :6784-6794

[3] Silver-mediated synthesis of heterocycles [J].

Alvarez-Corral, Miriam ;

Munoz-Dorado, Manuel ;

Rodirguez-Garcia, Ignacio .

CHEMICAL REVIEWS, 2008, 108 (08) :3174-3198

[4]

Badillo JJ, 2010, CURR OPIN DRUG DISC, V13, P758

[5] Recent Progress in Direct Introduction of Fluorinated Groups on Alkenes and Alkynes by means of C-H Bond Functionalization [J].

Besset, Tatiana ;

Poisson, Thomas ;

Pannecoucke, Xavier .

CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (51) :16830-16845

[6] Catalytic Asymmetric Michael Addition/Cyclization of Isothiocyanato Oxindoles: Highly Efficient and Versatile Approach for the Synthesis of 3,2'-Pyrrolidinyl Mono- and Bi-spirooxindole Frameworks [J].

Cao, Yi-Ming ;

Shen, Fang-Fang ;

Zhang, Fu-Ting ;

Wang, Rui .

CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (04) :1184-1188

[7] Chiral Bronsted acid-catalyzed diastereo- and enantioselective synthesis of CF3-substituted aziridines [J].

Chai, Zhuo ;

Bouillon, Jean-Philippe ;

Cahard, Dominique .

CHEMICAL COMMUNICATIONS, 2012, 48 (76) :9471-9473

[8] Asymmetric One-Pot Sequential Mannich/Hydroamination Reaction by Organo- and Gold Catalysts: Synthesis of Spiro[pyrrolidin-3,2′-oxindole] Derivatives [J].

Chen, Xianjie ;

Chen, Hui ;

Ji, Xun ;

Jiang, Hualiang ;

Yao, Zhu-Jun ;

Liu, Hong .

ORGANIC LETTERS, 2013, 15 (08) :1846-1849

[9] Organocatalytic Asymmetric Assembly Reactions: Synthesis of Spirooxindoles via Organocascade Strategies [J].

Cheng, Daojuan ;

Ishihara, Yoshihiro ;

Tan, Bin ;

Barbas, Carlos F., III .

ACS CATALYSIS, 2014, 4 (03) :743-762

[10] Recent advances in organocatalytic methods for the synthesis of disubstituted 2-and 3-indolinones [J].

Dalpozzo, Renato ;

Bartoli, Giuseppe ;

Bencivenni, Giorgio .

CHEMICAL SOCIETY REVIEWS, 2012, 41 (21) :7247-7290

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