Tetrahedron p. 11437 - 11454 (1999)
Update date:2022-08-05
Topics:
Dussault, Patrick H.
Han, Qiang
Sloss, Darby G.
Symonsbergen, David J.
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.
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