Enyne Metathesis (Enyne Bond Reorganization)

Steven T. Diver* and Anthony J. Giessert
Department of Chemistry, State University of New York at Buffalo, Amherst, New York 14260
Chem. Rev., 2004, 104 (3), pp 1317–1382
DOI: 10.1021/cr020009e
Publication Date (Web): March 10, 2004
Copyright © 2004 American Chemical Society

Table of Contents

  • 1. Introduction and Scope
  • 2. Mechanism Families
    • 2.1. Metal Salt-Catalyzed Enyne Bond Reorganization
    • 2.2. Metal Carbene-Mediated Enyne Metathesis2.2.1. Fischer Carbene Complex-Catalyzed Enyne Metathesis
  • 2.2.2. Enyne Metathesis with Ruthenium Carbenes
  • 3. Synthetic Applications
    • 3.1. Intramolecular Metathesis of Enynes3.1.1. Synthesis of Carbocycles and Various Heterocycles (O, N, P, Si) with Ring-Closing Enyne Metathesis
  • 3.1.2. β-Lactams through Ring-Closing Enyne Metathesis
  • 3.1.3. Unnatural Amino Acids Obtained through Ring-Closing Enyne Metathesis
  • 3.1.4. Carbohydrates in Ring-Closing Enyne Metathesis
  • 3.1.5. Medium- and Macro-Ring-Closing Enyne Metathesis
  • 3.1.6. Ring-Closing Enyne Metathesis with Element-Substituted Alkynes
  • 3.1.7. Natural Product Synthesis Employing Enyne Metathesis
    • 3.2. Intermolecular Enyne Cross Metathesis
  • 3.2.1 Reaction with Ethylene
  • 3.2.2. Cross Metathesis with Higher Alkenes
  • 3.2.3. Influence of Ethylene on Cross Metatheses
    • 3.3. Tandem Metathesis and Domino Metathesis
  • 4. Conclusion and Outlook
  • 5. Acknowledgments
  • 6. References

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History

  • Published In Issue March 10, 2004
  • Received June 5, 2003

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