N-Phosphorylated Pyrrolidines: An Overview of Synthetic Approaches

Andrey V. Smolobochkin; Almir S. Gazizov; Rakhymzhan A. Turmanov; Dinara S. Abdullaeva; Alexander R. Burilov; Michail A. Pudovik

doi:10.1055/s-0039-1690889

Synthesis, Table of Contents

Synthesis 2020; 52(15): 2162-2170
DOI: 10.1055/s-0039-1690889

short review

N-Phosphorylated Pyrrolidines: An Overview of Synthetic Approaches

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

,

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

,

Rakhymzhan A. Turmanov

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

^cKorkyt Ata Kyzylorda State University, 120014, Aiteke bike str., 29A, Kyzylorda, Republic of Kazakhstan

,

Dinara S. Abdullaeva

^dKazan Federal University, 420008, Kremlyovskaya str., 18, Kazan, Russian Federation

,

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

,

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

› Author Affiliations

Abstract

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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

Full Text

References

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