Synthesis and Reactivity of 1,2-Dioxolanes from β,γ-Epoxy
Ketones

Kandur, Wynne
V.; Richert, Kathleen J.; Rieder, Curtis J.; Thomas, Andrew M.; Hu, Chunhua; Ziller, Joseph W.; Woerpel, K. A.

doi:10.1021/ol500835f.s002

ol500835f_si_002.pdf (58.57 MB)

Synthesis and Reactivity of 1,2-Dioxolanes from β,γ-Epoxy Ketones

journal contribution

posted 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.