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Handbook of Metathesis: Second Edition

Catalyst-Controlled Stereoselective Olefin Metathesis

Publication ,  Chapter
Hoveyda, AH; Khan, RKM; Torker, S; Malcolmson, SJ
January 1, 2015

This chapter covers the advances made since 2003 in the development of catalysts that can control the stereochemical outcome of olefin metathesis reactions. Various enantioselective processes, such as enantioselective ring-opening/cross-metathesis (EROCM) and enantioselective ring-closing metathesis (ERCM), promoted by chiral Mo or Ru complexes are discussed. A more recent development has been the introduction of complexes that can deliver the (often) higher-energy Z-alkene products selectively (vs. the typically thermodynamically favored E-alkenes generated by previous catalyst systems). The mechanistic basis and utility of different Mo, W and Ru complexes that can be utilized to access linear or macrocyclic Z-olefins is detailed. In all cases, the advantages and shortcomings of different catalyst classes (e.g., Mo/W alkylidenes vs. Ru carbenes as well as different types within each system) and their symbiotic relationships are presented. Whenever possible, applications to synthesis of natural products are discussed to underscore utility.

Duke Scholars

DOI

ISBN

9783527334247

Publication Date

January 1, 2015

Volume

2-3

Start / End Page

503 / 562
 

Citation

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Hoveyda, A. H., Khan, R. K. M., Torker, S., & Malcolmson, S. J. (2015). Catalyst-Controlled Stereoselective Olefin Metathesis. In Handbook of Metathesis: Second Edition (Vol. 2–3, pp. 503–562). https://doi.org/10.1002/9783527674107.ch21
Hoveyda, A. H., R. K. M. Khan, S. Torker, and S. J. Malcolmson. “Catalyst-Controlled Stereoselective Olefin Metathesis.” In Handbook of Metathesis: Second Edition, 2–3:503–62, 2015. https://doi.org/10.1002/9783527674107.ch21.
Hoveyda AH, Khan RKM, Torker S, Malcolmson SJ. Catalyst-Controlled Stereoselective Olefin Metathesis. In: Handbook of Metathesis: Second Edition. 2015. p. 503–62.
Hoveyda, A. H., et al. “Catalyst-Controlled Stereoselective Olefin Metathesis.” Handbook of Metathesis: Second Edition, vol. 2–3, 2015, pp. 503–62. Scopus, doi:10.1002/9783527674107.ch21.
Hoveyda AH, Khan RKM, Torker S, Malcolmson SJ. Catalyst-Controlled Stereoselective Olefin Metathesis. Handbook of Metathesis: Second Edition. 2015. p. 503–562.
Journal cover image

DOI

ISBN

9783527334247

Publication Date

January 1, 2015

Volume

2-3

Start / End Page

503 / 562