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Synlett 1991; 1991(7): 517-519
DOI: 10.1055/s-1991-20785
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Modification of the Phosphorus Substituents in α-Chloromethylphosphonates as the Key to (E)-Selective Syntheses of α-Chlorinated Acrylic Esters

Carl Patois* , Philippe Savignac
  • *Laboratoire de Chimie du Phosphore et des Métaux de Transition, DCPH, École Polytechnique, F-91128 Palaiseau Cedex, France
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Publication Date:
07 March 2002 (online)

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3-Substituted ethyl 2-chloroacrylates can be prepared via a Horner-Emmons reaction of α-chlorophosphonocarboxylates with aldehydes in high yields with E stereoselectivities superior to 95 % if the α-chlorophosphonocarboxylate precursor is substituted by an N,N′ -dimethylethylenediamine group (2-chloromethyl-1,3-dimethyl-1,3,2-diazaphospholidin-2-one) and the reaction is carried out at -70 °C.

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