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The remarkable metal-catalysed olefin metathesis reaction

Nature volume 450, pages 243–251 (2007)Cite this article

Abstract

Catalytic olefin metathesis—through which pairs of C = C bonds are reorganized—transforms simple molecules to those that are complex and precious. This class of reactions has noticeably enriched chemical synthesis, which is the art of preparing scarce molecules with highly desirable properties (for example, medicinal agents or polymeric materials). Research in the past two decades has yielded structurally well-defined catalysts for olefin metathesis that are used to synthesize an array of molecules with unprecedented efficiency. Nonetheless, the full potential of olefin metathesis will be realized only when additional catalysts are discovered that are truly practical and afford exceptional selectivity for a significantly broader range of reactions.

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Figure 1: Different types of olefin metathesis.
Figure 2: Representative olefin metathesis catalysts.
Figure 3: The general mechanism for ring-closing olefin metathesis.
Figure 4: A concise synthesis of longithorone A.
Figure 5: General mechanism for catalytic ring-opening/cross metathesis.
Figure 6: Catalytic ring-opening/cross metathesis provides uniquely efficient pathways for synthesis of biologically active natural products.
Figure 7
Figure 8: Catalytic olefin metathesis has been used in the large-scale preparation of pharmaceutical candidates.
Figure 9: More recent and modified variants of Ru-based olefin metathesis catalysts 44–49 and an easier way to access a range of chiral Mo catalysts.

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Acknowledgements

Research in our laboratories regarding the development of catalysts for olefin metathesis has been funded by the US National Science Foundation and the US National Institutes of Health, Institute of General Medical Sciences.

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  1. Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, USA,

    Amir H. Hoveyda & Adil R. Zhugralin

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Hoveyda, A., Zhugralin, A. The remarkable metal-catalysed olefin metathesis reaction. Nature 450, 243–251 (2007). https://doi.org/10.1038/nature06351

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