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

Citation
P. Merino et al., 1,3-Dipolar cycloaddition between hetaryl nitrones and methyl acrylate: Theoretical study and application to the synthesis of functionalized pyrrolidines, HETEROCYCLE, 53(4), 2000, pp. 861-875
Citations number
71
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
HETEROCYCLES
ISSN journal
03855414 → ACNP
Volume
53
Issue
4
Year of publication
2000
Pages
861 - 875
Database
ISI
SICI code
0385-5414(20000401)53:4<861:1CBHNA>2.0.ZU;2-B
Abstract
The 1,3-dipolar cycloaddition reaction of N-benzyl-C-(hetaryl)nitrones gave preferentially trans-substituted 3,5-disubstituted isoxazolidines (endo ap proach) which can be further converted into the corresponding 5-hetaryl-3-h ydroxy-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.