Organocatalytic diastereoselective synthesis of spirooxindoles via [3+2] cycloadditions of azomethine ylides with α,β-unsaturated esters

被引：12

作者：

Penaska, Tibor ^{[1
]}

Ormandyova, Kristina ^{[1
]}

Meciarova, Maria ^{[1
]}

Filo, Juraj ^{[2
]}

Sebesta, Radovan ^{[1
]}

机构：

[1] Comenius Univ, Fac Nat Sci, Dept Organ Chem, Ilkovicova 6, Bratislava 84215, Slovakia

[2] Comenius Univ, Fac Nat Sci, Inst Chem, Ilkovicova 6, Bratislava 84215, Slovakia

来源：

NEW JOURNAL OF CHEMISTRY | 2017年 / 41卷 / 13期

关键词：

ASYMMETRIC 1,3-DIPOLAR CYCLOADDITION; ONE-POT; ALDEHYDES; CONSTRUCTION; DIVERSITY; PROLINE; SERVE;

D O I：

10.1039/c7nj00189d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient three-component organocatalytic cascade 1,3-dipolar cycloaddition reaction of in situ generated azomethine ylides with alpha,beta-unsaturated esters is described. This reaction afforded a small library comprised of 20 new highly substituted spirooxindole derivatives. The products were obtained in yields up to 76%, usually as single diastereomers. A range of different hydrogen bond donor, Bronsted basic or acidic organocatalysts were tested. Bifunctional thioureas and squaramides were identified as competent catalysts for this transformation. The effect of microwave irradiation, as well as solvent-free conditions, was also examined.

引用

页码：5506 / 5512

页数：7

共 50 条

[41] Expedient Synthesis of C-3-Ferrocenoyl-N-methylpyrrolidines via [3+2]-Cycloaddition Reaction of Azomethine Ylides
Sureshbabu, A. R.
Dhamodharan, V.
Raghunathan, R.
SYNTHETIC COMMUNICATIONS, 2009, 39 (16) : 2889 - 2894
[42] Highly enantioselective and diastereoselective [3+2] cycloadditions.
Xiang, BP
Davies, HML
Kong, N
Stafford, DG
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2002, 224 : U184 - U184
[43] Kinetic resolutions of azomethine imines via copper-catalyzed [3+2] cycloadditions
Suárez, A
Downey, CW
Fu, GC
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (32) : 11244 - 11245
[44] Asymmetric Synthesis of 3,3′-Tetrahydrofuryl Spirooxindoles via Palladium-Catalyzed [3+2] Cycloadditions of Methyleneindolinones with Vinylethylene Carbonates
Wang, Junwei
Zhao, Lei
Rong, Quanjin
Lv, Cheng
Lu, Yu
Pan, Xiang
Zhao, Lin
Hu, Lihong
ORGANIC LETTERS, 2020, 22 (15) : 5833 - 5838
[45] Synthesis of functionalized 2,5-dihydropyrrole derivatives via a convenient [3+2] annulation of azomethine ylides with allenoates
Huang, Zhusheng
Dai, Zonghao
Zhu, Jin
Yang, Fulai
Zhou, Qingfa
ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (36) : 6638 - 6646
[46] Diastereoselective Synthesis of Chiral 2,3-Disubstituted lndolines via Formal [3+2]-Cycloaddition of Arynes with γ-Amino-α,β-unsaturated Esters
Aher, Ravindra D.
Suryavanshi, Gurunath M.
Sudalai, Arumugam
JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (11): : 5940 - 5946
[47] Silver-Catalyzed [3+2] Cycloaddition of Azomethine Ylides with Isocyanides for Imidazole Synthesis
Hu, Zhongyan
Dong, Jinhuan
Xu, Xianxiu
ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (20) : 3585 - 3591
[48] Synthesis of Non-Racemic Pyrazolines and Pyrazolidines by [3+2] Cycloadditions of Azomethine Imines
Pozgan, Franc
Al Mamari, Hamad
Groselj, Uros
Svete, Jurij
Stefane, Bogdan
MOLECULES, 2018, 23 (01):
[49] Metal-catalyzed [3+2] cycloadditions of azomethine imines
Uroš Grošelj
Jurij Svete
Hamad H. Al Mamari
Franc Požgan
Bogdan Štefane
Chemistry of Heterocyclic Compounds, 2018, 54 : 214 - 240
[50] Intramolecular [3+2]-Cycloadditions of Azomethine Ylides Derived from Secondary Amines via Redox-Neutral C-H Functionalization
Mantelingu, Kempegowda
Lin, Yingfu
Seidel, Daniel
ORGANIC LETTERS, 2014, 16 (22) : 5910 - 5913

← 1 2 3 4 5 →