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Synthesis 2000; 2000(8): 1143-1147
DOI: 10.1055/s-2000-6324
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Synthesis of New Asymmetric Phosphonylated Thiazolines and their Use in Olefination Reactions

Nicolas Leflemme* , Patrice Marchand, Mihaela Gulea, Serge Masson
  • *Laboratoire de Chimie Moléculaire et Thioorganique, UMR 6507 CNRS, ISMRA-Université de Caen, 6 Bd. Maréchal Juin, 14050 Caen, France
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Publication Date:
31 December 2000 (online)

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N-(2-Hydroxyalkyl)-2-phosphonoethanethioamides were prepared from a readily accessible phosphonodithioacetate and commercial chiral β-amino alcohols. Taking advantage of both the presence of the hydroxy group (nucleofuge) and of the C=S (nucleophile) in the same molecule, we obtained new chiral phosphonylated thiazolines by an intramolecular cyclisation using the Mitsunobu procedure. These thiazoline-phosphonates were then involved in Horner-Wadsworth-Emmons reaction to give asymmetric vinylic thiazolines.

phosphonate - dithioester - thioamide - thiazoline - Mitsunobu reaction - Horner-Wadsworth-Emmons reaction

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