Synthesis 2020; 52(15): 2162-2170
DOI: 10.1055/s-0039-1690889
short review
© Georg Thieme Verlag Stuttgart · New York

N-Phosphorylated Pyrrolidines: An Overview of Synthetic Approaches

Andrey V. Smolobochkin
a  Arbuzov 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
,
a  Arbuzov 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
b  Kazan National Research Technological University, 420015, Karl Marx str., 68, Kazan, Russian Federation
c  Korkyt Ata Kyzylorda State University, 120014, Aiteke bike str., 29A, Kyzylorda, Republic of Kazakhstan
,
Dinara S. Abdullaeva
d  Kazan Federal University, 420008, Kremlyovskaya str., 18, Kazan, Russian Federation
,
Alexander R. Burilov
a  Arbuzov 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
a  Arbuzov 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
This work was supported by a grant from the President of the Russian Federation for support of young Russian scientists (Grant No. MD-585.2019.3).
Further Information

Publication History

Received: 18 February 2020

Accepted after revision: 15 March 2020

Publication Date:
14 April 2020 (online)


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

 
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