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Synlett 1992; 1992(6): 493-495
DOI: 10.1055/s-1992-21389
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Novel Synthesis of Chiral Allenyl Sulfoxides and Their Potential Use in Asymmetric Reactions

Elie Kerbage* , Max Malacria, Houda Fillion
  • *Laboratoire de Chimie Organique I, Associé CNRS URA 457, Université Claude Bernard, 43 Bd du 11 Novembre 1918, F-69622 Villeurbanne Cedex, France and Laboratoire de Chimie Organique, Institut des Sciences Pharmaceutiques et Biologiques, 8 Avenue Rockeffeller, F-69373 Lyon Cedex 08, France
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Publication Date:
08 March 2002 (online)

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Chiral allenyl sulfoxides 4 are prepared by substitution of allenyllithiums on (-)-(S)-menthyl p-tolylsulfinate (1). The reactions are performed at -115 °C by an inverse addition procedure. Their use in the asymmetric synthesis of 4,4-dialkyl-1-tert-butyl(or phenyl)-2-(p-toluenesulfinyl)-2, 3-butadien-1-ols 7 is described.