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Synthesis 1995; 1995(11): 1393-1396
DOI: 10.1055/s-1995-4123
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Functionalised α,β-Unsaturated Thioamides via Horner-Emmons Reactions

Sylvie Le Roy-Gourvennec, Serge Masson*
  • *Laboratoire de Chimie Moléculaire et Thioorganique (associé au CNRS), Université de Caen, Institut des Sciences de la Matière et du Rayonnement (ISMRa), 6 Bd du Maréchal Juin, F-14050 Caen, France, Fax +33(31)452877; email: masson@ismra.unicaen.fr
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Publication Date:
31 December 2000 (online)

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The reaction of a phosphonodithioacetate with amines (in particular functionalised amines) leads to thiocarbamoylmethylphosphonates (unsubstituted at the carbon α- to the phosphoryl group), which can be used as Horner-Emmons reagents. This pathway is a very convenient and general synthesis of functionalised thiocarbamoylphosphonates and α,β-unsaturated thioamides (in particular new amino acid derivatives).

phosphonates - dithioesters - α-unsaturated thioamides - Horner-Emmons olefination - amino acids