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DOI: 10.1055/s-1999-3378
The Syntheses and Properties of 1,2-Epoxyalkylphosphonates
Publikationsverlauf
Publikationsdatum:
31. Dezember 1999 (online)

This review article deals with the methods of preparation of dialkyl 1,2-epoxyalkylphosphonates 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.
Darzens reaction - halohydrins - halo ketones - fosfomycin - opening and rearrangement reactions