Synthesis of Phosphaproline Derivatives: A Short Overview

Almir S. Gazizov; Andrey V. Smolobochkin; Rahimjan A. Turmanov; Michail A. Pudovik; Alexander R. Burilov; Oleg G. Sinyashin

doi:10.1055/s-0037-1611891

Synthesis, Table of Contents

Synthesis 2019; 51(18): 3397-3409
DOI: 10.1055/s-0037-1611891

short review

Synthesis of Phosphaproline Derivatives: A Short Overview

Almir S. Gazizov ∗

^aArbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, 420088, Arbuzova str., 8, Kazan, Russian Federation Email: agazizov@iopc.ru

,

Andrey V. Smolobochkin

^aArbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, 420088, Arbuzova str., 8, Kazan, Russian Federation Email: agazizov@iopc.ru

,

Rahimjan A. Turmanov

^bKazan National Research Technological University, 420015, 68 Karl Marx str., Kazan, Russian Federation

,

Michail A. Pudovik

^aArbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, 420088, Arbuzova str., 8, Kazan, Russian Federation Email: agazizov@iopc.ru

,

Alexander R. Burilov

^aArbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, 420088, Arbuzova str., 8, Kazan, Russian Federation Email: agazizov@iopc.ru

,

Oleg G. Sinyashin

^aArbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, 420088, Arbuzova str., 8, Kazan, Russian Federation Email: agazizov@iopc.ru

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Abstract

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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

Full Text

References

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