Synthesis of α-Methylene-β-hydroperoxy Sulfoxides by Regioselective Photooxygenation (Schenck Reaction) of Racemic Vinyl Sulfoxides
作者:Waldemar Adam、A. Sampath Kumar、Chantu R. Saha-Möller
DOI:10.1055/s-1995-4138
日期:1995.12
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.