The Syntheses and Properties of 1,2-Epoxyalkylphosphonates

Bogdan Iorga (1) , Frédéric Eymery (1) , Philippe Savignac (1)

1 DCPH - Laboratoire Hétéroéléments et Coordination

The present review article deals with the methods of preparation of dialkyl 1,2epoxyalkylphosphonates as well as synthetically useful reactions of this class of compounds. Four main routes to 1,2-epoxyalkylphosphonates are described, in which new developments adapted to each processes are given, including the choice of the leaving group, new cyclisation methods and stereocontrol induction. Thermal and acid catalyzed rearrangements are also covered, and the use of the oxirane ring by nucleophilic opening is highlighted. Particular emphasis is placed on the synthetic approaches to antibiotic fosfomycin.

Mots clés: Darzens reaction; halohydrins; haloketones; fosfomycin; opening and rearrangement reactions

Domaines: Chimie organique

Bogdan Iorga, Frédéric Eymery, Philippe Savignac. The Syntheses and Properties of 1,2-Epoxyalkylphosphonates. Synthesis: Journal of Synthetic Organic Chemistry, 1999, 1999 (02), pp.207-224. ⟨10.1055/s-1999-3378⟩. ⟨hal-03161383⟩