Download PDF
Synthesis 2000; 2000(8): 1143-1147
DOI: 10.1055/s-2000-6324
paper
© 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.

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
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

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