Synthesis 2019; 51(18): 3397-3409
DOI: 10.1055/s-0037-1611891
short review
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Phosphaproline Derivatives: A Short Overview

a  Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, 420088, Arbuzova str., 8, Kazan, Russian Federation   Email: [email protected]
,
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: [email protected]
,
Rahimjan A. Turmanov
b  Kazan National Research Technological University, 420015, 68 Karl Marx str., Kazan, Russian Federation
,
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: [email protected]
,
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: [email protected]
,
Oleg G. Sinyashin
a  Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, 420088, Arbuzova str., 8, Kazan, Russian Federation   Email: [email protected]
› Author Affiliations
The work was supported by a grant from the President of the Russian Federation for support of young Russian scientists (MD-585.2019.3).
Further Information

Publication History

Received: 23 May 2019

Accepted after revision: 25 June 2019

Publication Date:
15 July 2019 (online)


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

 
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