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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 44, 2014 - Issue 9
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Original Articles

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

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Pages 1218-1226 | Received 24 Jun 2013, Published online: 28 Mar 2014
 

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

Notes

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

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