1,3-Dipolar cycloaddition between hetaryl nitrones and methyl acrylate: Theoretical study and application to the synthesis of functionalized pyrrolidines

被引：20

作者：

Merino, P ^{[1
]}

Anoro, S ^{[1
]}

Merchan, F ^{[1
]}

Tejero, T ^{[1
]}

机构：

[1] Univ Zaragoza, ICMA, Fac Ciencias, Dept Quim Organ, E-50009 Zaragoza, Spain

来源：

HETEROCYCLES | 2000年 / 53卷 / 04期

关键词：

isoxazclidine; 2-pyrrolidinone; MO calculation;

D O I：

10.3987/COM-99-8826

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The 1,3-dipolar cycloaddition reaction of N-benzyl-C-(hetaryl)nitrones gave preferentially trans-substituted 3,5-disubstituted isoxazolidines (endo approach) which can be further converted into the corresponding 5-hetaryl-3-hydroxy-2-pyrrolidinones. A theoretical study of the cycloaddition reaction by using both semiempirical (AM1, PM3) and ab initio (HF/3-21G, HF/6-31G*//3-21G) methods has also been carried out. In all cases the obtained results are in good qualitative agreement with the experimental observations.

引用

页码：861 / 875

页数：15