Photooxygenation of chiral dienol ethers: Asymmetric synthesis of alkoxydioxines

Article abstract of DOI:10.1016/S0040-4020(99)00666-3

The addition of ¹O₂ to chiral dienol ethers provides a new route to alkoxydioxines (alkoxyendoperoxides). Depending upon substitution and geometry, the [4+2] cycloaddition is accompanied or even supplanted by [2+2] cycloaddition leading to alkene cleavage and/or ene-like reaction leading to allylic hydroperoxides. The diastereoselectivity of cycloaddition is ultimately limited by the conformational freedom of the dienol ether substrates.