ol500835f_si_007.cif (12.18 kB)
Synthesis and Reactivity of 1,2-Dioxolanes from β,γ-Epoxy Ketones
datasetposted on 2014-05-16, 00:00 authored by Wynne V. Kandur, Kathleen J. Richert, Curtis J. Rieder, Andrew M. Thomas, Chunhua Hu, Joseph W. Ziller, K. A. Woerpel
Five-membered ring peroxides were prepared in one step in 31–86% yield from readily accessible β,γ-epoxy ketones and H2O2. The reaction proceeded via a tetrahydrofuran, which was converted to the thermodynamically favored 1,2-dioxolane. The product contains a leaving group, which can be displaced to synthesize analogues of the plakinic acid natural products.