Isatin N,N′-Cyclic Azomethine Imine 1,3-Dipole and Abnormal [3+2]-Cycloaddition with Maleimide in the Presence of 1,4-Diazabicyclo[2.2.2]octane

被引：61

作者：

Wang, Xiao ^{[1
,2
]}

Yang, Peng ^{[1
,2
]}

Zhang, Yong ^{[1
,2
]}

Tang, Chao-Zhe ^{[1
,2
]}

Tian, Fang ^{[1
]}

Peng, Lin ^{[1
]}

Wang, Li-Xin ^{[1
]}

机构：

[1] Chinese Acad Sci, Chengdu Inst Organ Chem, Key Lab Asymmetr Synth & Chirotechnol Sichuan Pro, Chengdu 610041, Peoples R China

[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 03期

关键词：

ASYMMETRIC TOTAL-SYNTHESIS; CHIRAL LEWIS-ACID; 3+2 CYCLOADDITION; CARBONYL YLIDES; DIPOLAR CYCLOADDITION; NITRONES; CONSTRUCTION; HETEROCYCLES; DERIVATIVES; FRAMEWORKS;

D O I：

10.1021/acs.orglett.6b03815

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new isatin N,N'-cyclic azomethine imine synthon was devised, and an unexpected abnormal [3 + 2]-cycloaddition with maleimide catalyzed by 1,4-diazabicyclo[2.2.2]octane (DABCO) has been disclosed. A variety of tricyclic spiropyrrolidine oxindoles bearing a dinitrogen heterocycle and succinimide scaffold were obtained in excellent yields (up to 96%) and diastereoselectivities (up to 97:3) under mild conditions.

引用

页码：646 / 649

页数：4

共 69 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] APPLICATION OF THE HYPERSURFACE ITERATIVE PROJECTION METHOD TO BICYCLIC PYRAZOLIDINONE ANTIBACTERIAL AGENTS [J].

BOYD, DB .

JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (10) :1443-1449

[3] Enantioselective 1,3-dipolar cycloaddition of cyclic enones catalyzed by multifunctional primary amines: Beneficial effects of hydrogen bonding [J].

Chen, Wei ;

Du, Wei ;

Duan, Yong-Zheng ;

Wu, Yong ;

Yang, Sheng-Yong ;

Chen, Ying-Chun .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (40) :7667-7670

[4] Organocatalytic and stereoselective [3+2] cycloadditions of azomethine imines with α,β-unsaturated aldehydes [J].

Chen, Wei ;

Yuan, Xiang-Hong ;

Li, Rui ;

Du, Wei ;

Wu, Yong ;

Ding, Li-Sheng ;

Chen, Ying-Chun .

ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (14) :1818-1822

[5] Intramolecular dipolar cycloaddition reactions of azomethine ylides [J].

Coldham, I ;

Hufton, R .

CHEMICAL REVIEWS, 2005, 105 (07) :2765-2809

[6] 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

[7] Structure-based design of spiro-oxindoles as potent, specific small-molecule inhibitors of the MDM2-p53 interaction [J].

Ding, Ke ;

Lu, Yipin ;

Nikolovska-Coleska, Zaneta ;

Wang, Guoping ;

Qiu, Su ;

Shangary, Sanjeev ;

Gao, Wei ;

Qin, Dongguang ;

Stuckey, Jeanne ;

Krajewski, Krzysztof ;

Roller, Peter P. ;

Wang, Shaomeng .

JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (12) :3432-3435

[8] [3+3]-Cycloaddition Reactions of α-Acidic Isocyanides with 1,3-Dipolar Azomethine Imines [J].

Du, Juan ;

Xu, Xianxiu ;

Li, Yifei ;

Pan, Ling ;

Liu, Qun .

ORGANIC LETTERS, 2014, 16 (15) :4004-4007

[9] Highly Diastereoselective DABCO-Catalyzed [3+3]-Cycloaddition of 1,4-Dithiane-2,5-diol with Azomethine Imines [J].

Fang, Xin ;

Li, Jun ;

Tao, Hai-Yan ;

Wang, Chun-Jiang .

ORGANIC LETTERS, 2013, 15 (21) :5554-5557

[10] 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

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