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

doi:10.1021/ol500835f

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

Chemistry

Research output: Contribution to journal › Article › peer-review

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 language	English (US)
Pages (from-to)	2650-2653
Number of pages	4
Journal	Organic Letters
Volume	16
Issue number	10
DOIs	https://doi.org/10.1021/ol500835f
State	Published - May 16 2014

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol500835f

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

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.",

author = "Kandur, {Wynne V.} and Richert, {Kathleen J.} and Rieder, {Curtis J.} and Thomas, {Andrew M.} and Chunhua Hu and Ziller, {Joseph W.} and Woerpel, {K. A.}",

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T1 - Synthesis and reactivity of 1,2-dioxolanes from β,γ-epoxy ketones

AU - Kandur, Wynne V.

AU - Richert, Kathleen J.

AU - Rieder, Curtis J.

AU - Thomas, Andrew M.

AU - Hu, Chunhua

AU - Ziller, Joseph W.

AU - Woerpel, K. A.

PY - 2014/5/16

Y1 - 2014/5/16

N2 - 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.

AB - 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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JO - Organic Letters

JF - Organic Letters

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

Abstract

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