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Asymmetric copper-catalyzed

McMillen1, Varga, Reed

  • 1Department of Chemistry, Indiana University, South Bend 46634-7111, USA.

The Journal of Organic Chemistry
|May 2, 2000
PubMed
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The asymmetric copper-catalyzed rearrangement of sulfur ylides is highly sensitive to the allyl sulfide structure. Optimal results were achieved with specific alkyl and aryl substituents, demonstrating significant asymmetric induction.

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Asymmetric Synthesis

Background:

  • Sulfur ylides are versatile intermediates in organic synthesis.
  • Asymmetric catalysis enables the selective formation of chiral molecules.
  • Copper-catalyzed reactions offer efficient pathways for C-C and C-heteroatom bond formation.

Purpose of the Study:

  • To investigate the influence of allyl sulfide structure on copper-catalyzed asymmetric [2,3]-sigmatropic rearrangement.
  • To explore the impact of alkyl and aryl substituents on enantioselectivity.
  • To optimize reaction conditions for high asymmetric induction.

Main Methods:

  • Asymmetric copper-catalyzed reaction of various substituted allyl sulfides with ethyl diazoacetate.
  • Utilized copper triflate (CuOTf) and C2-symmetric bis-oxazoline ligands.

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  • Determined enantioselectivity using NMR spectroscopy.

    • Main Results:

    • Asymmetric induction varied significantly based on allyl sulfide structure, ranging from 2.8% to 60% ee.
    • The stereochemistry of specific products was confirmed via NMR.
    • Electronic properties of aryl substituents influenced enantioselectivity, with electron-donating groups showing lower ee.

    Conclusions:

    • The structure of the starting allyl sulfide is a critical factor in achieving high enantioselectivity in copper-catalyzed [2,3]-sigmatropic rearrangements.
    • Chiral auxiliaries, like the menthyl group, can significantly enhance asymmetric induction.
    • Further studies can explore a wider range of substrates and catalytic systems.