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Related Experiment Videos

[Stereoselective epoxidation with bulky dioxiranes generated from substituted cyclohexanones].

M Kurihara1, N Miyata

  • 1masaaki@nihs.go.jp

Kokuritsu Iyakuhin Shokuhin Eisei Kenkyujo Hokoku = Bulletin of National Institute of Health Sciences
|March 31, 1999
PubMed
Summary
This summary is machine-generated.

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Sterically hindered ketones generate bulky dioxiranes for stereoselective epoxidation. A basic CH2Cl2-MeOH buffer system enhances yields and trans-selectivity for olefins and acyclic silyl ethers.

Area of Science:

  • Organic Chemistry
  • Oxidation Reactions

Context:

  • Dioxiranes are versatile oxidants generated from potassium monoperoxysulfate (KHSO5) and ketones.
  • Dimethyldioxirane from acetone is widely used, but dioxiranes from other ketones are less explored.
  • Hindered dioxiranes are predicted to act as bulky oxidants for stereoselective epoxidation.

Purpose:

  • To investigate the stereoselective epoxidation of olefins and acyclic silyl ethers using dioxiranes derived from sterically hindered ketones.
  • To optimize reaction conditions for improved yields and selectivity compared to existing methods.

Summary:

  • Epoxidations using hindered alpha-substituted cyclohexanones under neutral conditions yielded low results.
  • A basic CH2Cl2-MeOH buffer system (pH 11) proved effective for epoxidation of olefins with Oxone and substituted cyclohexanones.

Related Experiment Videos

  • High trans-selectivities were achieved for cyclohexen derivatives, and erythro epoxides were stereoselectively formed from acyclic silyl ethers.

    • Impact:

    • Establishes an effective method for stereoselective epoxidation using hindered dioxiranes.
    • Expands the synthetic utility of dioxiranes derived from less common ketones.
    • Provides a valuable tool for synthesizing complex epoxides with high stereochemical control.