Synlett 2015; 26(20): 2745-2750
DOI: 10.1055/s-0035-1560178
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© Georg Thieme Verlag Stuttgart · New York

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

Jundong Li
Department of Chemistry and Fujian Provincial Key Laboratory of Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, P. R. of China   Email: ydzhang@xmu.edu.cn
,
Huaibo Zhao
Department of Chemistry and Fujian Provincial Key Laboratory of Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, P. R. of China   Email: ydzhang@xmu.edu.cn
,
Yandong Zhang*
Department of Chemistry and Fujian Provincial Key Laboratory of Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, P. R. of China   Email: ydzhang@xmu.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 06 July 2015

Accepted after revision: 02 August 2015

Publication Date:
02 September 2015 (online)

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

 
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