Catalyst-Controlled Stereoselective Olefin Metathesis

Book Section

© 2015 Wiley-VCH Verlag GmbH & Co. KGaA. All rights reserved. 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.

Full Text

Duke Authors

Cited Authors

  • Hoveyda, AH; Khan, RKM; Torker, S; Malcolmson, SJ

Published Date

  • January 1, 2015

Volume / Issue

  • 2-3 /

Book Title

  • Handbook of Metathesis: Second Edition

Start / End Page

  • 503 - 562

International Standard Book Number 13 (ISBN-13)

  • 9783527674107

Digital Object Identifier (DOI)

  • 10.1002/9783527674107.ch21

Citation Source

  • Scopus