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

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