Synthesis and reactivity of 1,2-dioxolanes from β,γ-epoxy ketones

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

Research output: Contribution to journalArticle

Abstract

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.

Original languageEnglish (US)
Pages (from-to)2650-2653
Number of pages4
JournalOrganic Letters
Volume16
Issue number10
DOIs
StatePublished - May 16 2014

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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  • Cite this

    Kandur, W. V., Richert, K. J., Rieder, C. J., Thomas, A. M., Hu, C., Ziller, J. W., & Woerpel, K. A. (2014). Synthesis and reactivity of 1,2-dioxolanes from β,γ-epoxy ketones. Organic Letters, 16(10), 2650-2653. https://doi.org/10.1021/ol500835f