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Synthesis 1995; 1995(12): 1525-1528
DOI: 10.1055/s-1995-4138
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Synthesis of α-Methylene-β-hydroperoxy Sulfoxides by Regioselective Photooxygenation (Schenck Reaction) of Racemic Vinyl Sulfoxides

Waldemar Adam* , A. Sampath Kumar, Chantu R. Saha-Möller
  • *Institute of Organic Chemistry, University of Würzburg, Am Hubland, D-97074 Würzburg, Germany, Fax +49(931)8884756; E-mail Adam@vax.rz.uni-wuerzburg.d400.de
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Publikationsdatum:
31. Dezember 2000 (online)

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The β-hydroperoxy vinyl sulfoxides 3 were synthesized in good to excellent yields by regioselective photooxygenation of racemic vinyl sulfoxides 2. Moderate diastereoselectivities were observed in the ene reaction of singlet oxygen (Schenck Reaction) with the E- or Z-vinyl sulfoxides 2e. Titanium-catalyzed oxygen transfer reaction of these sulfoxy-functionalized racemic allylic hydroperoxides 3 resulted chemoselectively in the corresponding sulfones 5.

α-methylene-β-hydroxy sulfoxide - α-methylene-β-hydroxysulfone - synthesis - singlet oxygen ene reaction - titanium-catalyzed oxygen transfer