One-Pot, Three-Component Cycloaddition of Nonstabilized Azomethine Ylides to β-Nitrostyrene, a Highly Electron Deficient Dipolarophile

Abstract

A facile route to tetra-substituted pyrrolidines has been accomplished by 1,3-dipolar cycloaddition reaction. Several pyrrolidine compounds have significant biological activity. A highly electron-deficient dipolarophile, β-nitrostyrene, was reacted with nonstabilized azomethine ylides derived from aryl aldehyde and L-phenylglycine in dry dimethyl formanide. The structures and stereochemistry of the cycloadducts were established by infrared, NMR spectroscopy, and single-crystal x-ray crystallographic analyses.

GRAPHICAL ABSTRACT

Keywords:

• 1,3-Dipolar cycloaddition
• β-nitrostyrene
• nonstabilized azomethine ylides
• tetra-substituted pyrrolidine

Notes

^{a, b} Yield and the ratio of the cycloadducts were determined from the crude ¹H NMR spectra.