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Synthesis 1997; 1997(6): 653-656
DOI: 10.1055/s-1997-1401
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Efficient and Stereoselective One-Pot Syntheses of Diethyl (Z)- or (E)-1-Alkylidene-3-oxobutylphosphonates

Abdourahman Mohamed-Hachi, Elie About-Jaudet, Jean-Claude Combret, Noël Collignon*
  • *Laboratoire d’Hétérochimie Organique de l’IRCOF, Université de Rouen-INSAR, Place E. Blondel, BP 08, F-76131 Mont-Saint-Aignan Cedex, France, Fax +(33)0235528379; E-mail: Noel.Collignon@insa-rouen.fr
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Publication Date:
31 December 2000 (online)

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Two one-pot procedures starting from diethyl 3,3-diethoxybutyl-phosphanate and aldehydes are proposed for the stereoselective synthesis of the title compounds. In the first one, the use of a Peterson reagent generated in situ, leads to a high (Z)-stereoselective olefination process. In the second, a base-induced 1,2-elimination reaction of a phosphate derivative controls the (E)-stereoselective formation of the double bond.

α-alyklidene - γ-oxo phosphonates - stereoselective olefination processes - one-pot syntheses