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Related Experiment Videos

Trans-diaryl epoxides: asymmetric synthesis, ring-opening, and absolute configuration.

A Solladié-Cavallo1, M Roje, M Giraud-Roux

  • 1Laboratoire de stéréochimie organométallique associé au CNRS, ECPM/Université L. Pasteur, 25 rue Becquerel, 67087 Strasbourg, France. cavallo@chimie.u-strasbg.fr

Chirality
|February 11, 2004
PubMed
Summary

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Chiral aryl epoxides were synthesized with high purity. The CD exciton chirality method determined their absolute configurations, confirming asymmetric synthesis strategies.

Area of Science:

  • Organic Chemistry
  • Stereochemistry
  • Chiral Synthesis

Background:

  • Asymmetric synthesis of epoxides is crucial for producing enantiomerically pure compounds.
  • Establishing absolute configurations of chiral molecules requires reliable methodologies.

Purpose of the Study:

  • To synthesize anthryl-phenyl, phenanthryl-phenyl, and naphthyl-phenyl trans-epoxides with high enantiomeric purity.
  • To determine the absolute configurations of these epoxides using the CD exciton chirality method.
  • To validate previous findings on asymmetric synthesis and clarify steric interactions in chiral assignment.

Main Methods:

  • Synthesis of enantiopure sulfonium salts derived from Eliel's oxathiane.
  • Asymmetric synthesis of trans-epoxides.
  • Epoxide ring opening with lithium aluminum hydride (LiAlH(4)) to form alcohols.

Related Experiment Videos

  • Determination of absolute configurations using the Circular Dichroism (CD) exciton chirality method with a Zn-porphyrin tweezer.

    • Main Results:

    • Synthesis of trans-epoxides (1, 2, and 3) with enantiomeric purities of 95%, 99%, and 96%, respectively.
    • Determination of (1R,2R) absolute configurations for the synthesized epoxides.
    • Confirmation of the R-configuration at C2 for (-)-1, (+)-2, and (-)-3, consistent with prior studies.
    • Assignment of (1S,2R)-configuration for the cis isomer when present.
    • Clarification of relative steric sizes of phenyl and CH(2)-aryl groups (phenyl=medium, anthracenyl CH(2) and phenanthryl CH(2)=large) through agreement between molecular modeling and CD spectra.

    Conclusions:

    • The study successfully synthesized and determined the absolute configurations of novel chiral aryl epoxides.
    • The CD exciton chirality method, employing a Zn-porphyrin tweezer, proved effective for assigning absolute configurations.
    • The findings reinforce the utility of asymmetric synthesis strategies and provide insights into steric factors critical for chiral recognition.