Radical-Induced Epoxide Fragmentation Chemistry. n-Bu3Sn* Radical Catalyzed Isomerization of Epoxyketones to Carbocycles

Article abstract of DOI:10.1016/S0040-4039(00)60475-6

Cyclic α,β-epoxyketones are converted to bi- or tricyclic β-hydroxyketones in the presence of n-Bu3Sn* radical.Addition of n-Bu3Sn* to carbonyl group gives a ketyl radical that triggers the epoxide fragmentation which is then followed by a 1,5-hydrogen ab