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, Keith 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

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Dioxolanes
Peroxides
Biological Products
Ketones
ketones
reactivity
Acids
peroxides
synthesis
products
tetrahydrofuran
analogs
acids
rings
formal glycol

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

Kandur, W. V., Richert, K. J., Rieder, C. J., Thomas, A. M., Hu, C., Ziller, J. W., & Woerpel, K. (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

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, Keith.

In: Organic Letters, Vol. 16, No. 10, 16.05.2014, p. 2650-2653.

Research output: Contribution to journalArticle

Kandur, WV, Richert, KJ, Rieder, CJ, Thomas, AM, Hu, C, Ziller, JW & Woerpel, K 2014, 'Synthesis and reactivity of 1,2-dioxolanes from β,γ-epoxy ketones', Organic Letters, vol. 16, no. 10, pp. 2650-2653. https://doi.org/10.1021/ol500835f
Kandur WV, Richert KJ, Rieder CJ, Thomas AM, Hu C, Ziller JW et al. Synthesis and reactivity of 1,2-dioxolanes from β,γ-epoxy ketones. Organic Letters. 2014 May 16;16(10):2650-2653. https://doi.org/10.1021/ol500835f
Kandur, Wynne V. ; Richert, Kathleen J. ; Rieder, Curtis J. ; Thomas, Andrew M. ; Hu, Chunhua ; Ziller, Joseph W. ; Woerpel, Keith. / Synthesis and reactivity of 1,2-dioxolanes from β,γ-epoxy ketones. In: Organic Letters. 2014 ; Vol. 16, No. 10. pp. 2650-2653.
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