Synthesis of Phosphaproline Derivatives: A Short Overview

Abstract

Pyrrolidine-based phosphonates, analogues of the natural amino acid proline, possess a diverse set of biological activity. The goal of this short review is to summarize the major developments in the synthesis of phosphaproline derivatives reported since 2004 with special emphasis on the mechanisms and limitations of the methods presented.

1 Introduction

2 Phosphorylation of Pyrrolidine Derivatives

2.1 Syntheses via Pudovik Reaction

2.2 Syntheses via Arbuzov Reaction

2.3 Decarboxylative Phosphorylation of Proline

2.4 Direct C–H Bond Phosphorylation

2.5 Other Reactions

2.6 Overview of Phosphorylation Methods

3 Synthesis of 2-Phosphorylpyrrolidines from Acyclic Precursors

3.1 Cyclization of 4-Substituted Butylamine Derivatives

3.2 [3+2]-Dipolar Cycloaddition of α-Iminophosphonates

3.3 Cyclization of Aminoalkynes and 4-Aminocarbonyl Compounds

4 Conclusions

Key words

phosphorylation - pyrrolidines - phosphaproline - heterocycles - Arbuzov reaction - Pudovik reaction - cycloaddition

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