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