Recent Progress in the Synthesis of 5-Unsubstituted Pyrrolidines via [3+2] Cycloadditions

Dedicated to Professor Pei-Qiang Huang

Abstract

The 1,3-dipolar cycloaddition of azomethine ylides with alkenes is one of the most powerful methods for the synthesis of multisubstituted pyrrolidines. 5-Unsubstituted pyrrolidines are important structural motifs of numerous biologically active natural products and drugs. Herein, recent progress in the synthesis of 5-unsubstituted pyrrolidines through intermolecular [3+2] cycloaddition is highlighted.

1 Introduction

2 Recent Development with α-Silylimines as Azomethine Ylide Precursors

3 Two-Step Protocol with α-Iminonitriles as Azomethine Ylide Precursors

4 Applications to Total Synthesis

5 Summary

Key words

cycloaddition - heterocycles - asymmetric catalysis - ylides - alkaloids

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