The Syntheses and Properties of 1,2-Epoxyalkylphosphonates

Bogdan Iorga; Frédéric Eymery; Philippe Savignac

doi:10.1055/s-1999-3378

Synthesis 1999; 1999(2): 207-224
DOI: 10.1055/s-1999-3378

review

© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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

Abstract

PDF Download All articles of this category

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

PDF (373 kb)