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Synlett 1992; 1992(10): 825-826
DOI: 10.1055/s-1992-22017
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A Convenient Method for the Preparation of 1-(Phenylsulfonyl)-1-alkynes

Martin C. Clasby* , Donald Craig
  • *Department of Chemistry, Imperial College of Science, Technology and Medicine, London SW7 2AY, England
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Publication Date:
08 March 2002 (online)

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A three-step procedure for the synthesis of 1-(phenylsulfonyl)-1-alkynes is described. The method involves preparation of β-ketosulfones 2 either by addition of lithio(phenylsulfonyl)methane to ε-caprolactone followed by hydroxyl protection. Subsequent treatment with triflic anhydride-Hünig's base gives 1-(phenylsulfonyl)-1-alkynes 3 in good overall yield. Tetrahydropyranyl, benzyl and t-butyldimethylsilyl ethers, and acetate esters are tolerant of the reaction conditions.