N-Phosphorylated Pyrrolidines: An Overview of Synthetic Approaches

Abstract

Organophosphorus pyrrolidine derivatives possessing P–N bonds are a promising yet underexplored class of compounds. In this short review we overview the general approaches to these compounds described so far, with a special emphasis on their asymmetric synthesis.

1 Introduction

2 Synthesis of Pyrrolidine-Based P(III) Derivatives

3 Synthesis of Pyrrolidine-Based P(V) Derivatives

3.1 Phosphorylation of Pyrrolidines with P(V) Acid Chlorides

3.2 Phosphorylation of Pyrrolidines with P(V) Acid Esters

3.3 Syntheses via the Atherton–Todd Reaction

3.4 Oxidation of Pyrrolidine-Based P(III) Derivatives

4 Syntheses of N-Phosphorylpyrrolidines from Acyclic Precursors

5 Conclusions

Key words

phosphorylation - Atherton–Todd reaction - pyrrolidines - heterocycles - phosphoramides

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