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Related Experiment Videos

Efficient Synthesis of Functionalized [7]Helicenes.

Joseph M. Fox1, Naomi R. Goldberg, Thomas J. Katz

  • 1Department of Chemistry, Columbia University, New York, New York 10027.

The Journal of Organic Chemistry
|October 24, 2001
PubMed
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Conversion of a [6]Helicene into an [8]Helicene and a Helical 1,10-Phenanthroline Ligand.

The Journal of organic chemistry·2001
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Easy Synthesis of Functionalized Hetero[7]helicenes.

The Journal of organic chemistry·2001
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Researchers synthesized [7]helicenebisquinones efficiently using silyl enol ethers and p-benzoquinone. This method provides a scalable route to these complex molecules, which are readily resolved into enantiomers.

Area of Science:

  • Organic Chemistry
  • Stereochemistry
  • Asymmetric Synthesis

Background:

  • Helicenes are polycyclic aromatic hydrocarbons with a unique helical structure.
  • Chiral helicenes are of interest in materials science and asymmetric catalysis.
  • Efficient synthesis and resolution of helicene derivatives remain a challenge.

Purpose of the Study:

  • To develop a facile and scalable synthetic route to [7]helicenebisquinones.
  • To investigate the utility of silyl enol ethers in helicene synthesis.
  • To achieve efficient enantiomeric resolution and absolute configuration assignment of the synthesized helicenes.

Main Methods:

  • Reaction of silyl enol ethers derived from 9,10-disiloxy-3,6-diacetylphenanthrene with p-benzoquinone.
  • Comparison of silyl enol ethers with ethyl enol ethers for the synthesis.

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  • Chiral chromatography for enantiomeric resolution.
  • Spectroscopic methods for absolute configuration assignment.

    • Main Results:

    • [7]Helicenebisquinones were synthesized in good yield and quantity.
    • Silyl enol ethers proved superior to ethyl enol ethers, yielding significantly higher product.
    • Efficient separation of enantiomers was achieved.
    • Absolute configurations of the helicene enantiomers were successfully assigned.

    Conclusions:

    • The developed method offers a straightforward and scalable approach for synthesizing [7]helicenebisquinones.
    • Silyl enol ether chemistry is highly effective for constructing the helicene framework.
    • The efficient resolution and configuration assignment pave the way for their application in chiral technologies.