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Synlett 1991; 1991(7): 509-510
DOI: 10.1055/s-1991-20781
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Development of a New ß-Acylvinyl Anion Equivalent from 1-(Methylsulfinyl)alka-1,2-dienes

Jean-Bernard Baudin* , Sylvestre A. Julia, Robert Lorne
  • *Laboratoire de Chimie, Ecole Normale Supérieure, 24 rue Lhomond, F-75231 Paris Cedex 05, France
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Publication Date:
07 March 2002 (online)

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By deprotonation with methyllithium or lithium diisopropylamide and reaction with alkyl halides, the allenic methyl sulfoxides 2 [1-(methylsulfinyl)alka-1,2-dienes] have been converted into substituted propargylic sulfoxides 5 [1,3-disubstituted 1-(methylsulfinyl)-2-alkynes]. Smooth desulfurization of 5 using 2-mercapto-1-methylimidazole furnished the corresponding conjugated enones 9.