Mg-Promoted Stereoselective Desulfonation of β-Arylvinyl Sulfone Derivatives

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  • Ikuzo Nishiguchi
    Department of Chemistry, Nagaoka University of Technology1603-1 Kamitomioka-cho, Nagaoka, Niigata
  • Takeshi Matsumoto
    Department of Chemistry, Nagaoka University of Technology1603-1 Kamitomioka-cho, Nagaoka, Niigata
  • Takeshi Kuwahara
    Department of Chemistry, Nagaoka University of Technology1603-1 Kamitomioka-cho, Nagaoka, Niigata
  • Makoto Kyoda
    Department of Chemistry, Nagaoka University of Technology1603-1 Kamitomioka-cho, Nagaoka, Niigata
  • Hirofumi Maekawa
    Department of Chemistry, Nagaoka University of Technology1603-1 Kamitomioka-cho, Nagaoka, Niigata

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<jats:title>Abstract</jats:title> <jats:p>β-Arylvinyl p-tolylsulfones, easily prepared from base-catalyzed condensation of aromatic aldehydes with a variety of p-tolylsulfones, were efficiently transformed to the corresponding (E)-β-substituted aromatic olefins in a stereoselective manner through Mg-promoted reduction. The reaction may be initiated through electron transfer from Mg metal to the vinyl sulfones to give the corresponding anionic species followed by stereoselective elimination of a sulfonyl group.</jats:p>

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  • Chemistry Letters

    Chemistry Letters 31 (4), 478-479, 2002-04-01

    Oxford University Press (OUP)

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