Synthesis and Reactivity of 1,2-Dioxolanes from β,γ-Epoxy Ketones
journal contributionposted on 16.05.2014, 00:00 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.