Synthesis and Reactivity of 1,2-Dioxolanes from β,γ-Epoxy Ketones
2014
Kandur, Wynne V. | Richert, Kathleen J. | Rieder, Curtis J. | Thomas, Andrew M. | Hu, Chunhua | Ziller, Joseph W. | Woerpel, K. A.
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.
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