Stereoselective synthesis of α-hydroxyphosphonates, a literature review

Enantiopure α-hydroxyphosphonates represent an important class of organophosphorus compounds that have received much attention due to their diverse biological and synthetic applications. This review provides a comprehensive overview of enantioselective methods for the synthesis of chiral α-hydroxyphosphonates, covering the literature from 1983 to February 2024. It describes the main synthetic strategies, in particular the asymmetric hydrophosphonylation of carbonyl compounds, the asymmetric reduction of α-ketophosphonates and α,β-phosphonoenolates. In addition, the review investigates the strengths and weaknesses of each method, and provides detailed insights into reaction conditions, substrate scope, and enantiomeric excesses.

Abstract

Due to their role in drug design and as building blocks, enantiopure α-hydroxyphosphonates are at the forefront of contemporary research. Over the past decades, synthetic methods have been developed that highlight the clear interest and practical importance of these compounds. This review aims to provide an up-to-date overview of the synthesis of chiral α-hydroxyphosphonates, covering the literature from its inception in 1983 to February 2024.