Synthesis of Phosphaproline Derivatives: A Short Overview

• DOI: 10.1055/s-0037-1611891
• Publication Date: 2019-07-15T18:51:27Z
• Authors: Almir S. Gazizov; Andrey V. Smolobo...; Rahimjan A. Turmanov; Michail A. Pudovik; Alexander R. Burilov; Oleg G. Sinyashin
• Keywords: 01 natural sciences; 0104 chemical sciences

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 Introduction2 Phosphorylation of Pyrrolidine Derivatives2.1 Syntheses via Pudovik Reaction2.2 Syntheses via Arbuzov Reaction2.3 Decarboxylative Phosphorylation of Proline2.4 Direct C–H Bond Phosphorylation2.5 Other Reactions2.6 Overview of Phosphorylation Methods3 Synthesis of 2-Phosphorylpyrrolidines from Acyclic Precursors3.1 Cyclization of 4-Substituted Butylamine Derivatives3.2 [3+2]-Dipolar Cycloaddition of α-Iminophosphonates3.3 Cyclization of Aminoalkynes and 4-Aminocarbonyl Compounds4 Conclusions