1,3-Dipolar Cycloadditions of N-Benzyl Furfuryl Nitrones with Electron-rich Alkenes

Abstract

The 1,3-dipolar cycloaddition reaction of N-benzyl-C-(2-furyl)nitrones with electron-rich alkenes gives preferentially trans-substituted 3,5-disubstituted isoxazolidines (endo approach). These experimental results are in good qualitative agreement with the predicted ones by semiempirical (AM1 and PM3) and ab initio (HF/3-21G) methods.

Keywords

• Nitrones
• isoxazolidines
• pyrrolidines
• theoretical calculations
• cycloaddition