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Synthesis 1999; 1999(2): 207-224
DOI: 10.1055/s-1999-3378
review
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The Syntheses and Properties of 1,2-Epoxyalkylphosphonates

Bogdan Iorga* , Frédéric Eymery, Philippe Savignac
  • *Laboratoire Hétéroéléments et Coordination, UMR CNRS 7653, Ecole Polytechnique, 91128 Palaiseau Cedex, France; Fax +33(1)69 33 39 90; E-mail: dcph@poly.polytechnique.fr
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Publication Date:
31 December 1999 (online)

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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