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Published September 4, 2017 | Accepted Version
Journal Article Open

Stereoretentive Olefin Metathesis: An Avenue to Kinetic Selectivity


Olefin metathesis is an incredibly valuable transformation that has gained widespread use in both academic and industrial settings. Lately, stereoretentive olefin metathesis has garnered much attention as a method for the selective generation of both E- and Z-olefins. Early studies employing ill-defined catalysts showed evidence for retention of the stereochemistry of the starting olefins at low conversion. However, thermodynamic ratios E/Z were reached as the reaction proceeded to equilibrium. Recent studies in olefin metathesis have focused on the synthesis of catalysts that can overcome the inherent thermodynamic preference of an olefin, providing synthetically useful quantities of a kinetically favored olefin isomer. These reports have led to the development of stereoretentive catalysts that not only generate Z-olefins selectively, but also kinetically produce E-olefins, a previously unmet challenge in olefin metathesis. Advancements in stereoretentive olefin metathesis using tungsten, ruthenium, and molybdenum catalysts are presented.

Additional Information

© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. Accepted manuscript online: 9 June 2017; Manuscript Accepted: 9 June 2017; Manuscript Revised: 8 June 2017; Manuscript Received: 6 May 2017. Acknowledgements are made to the National Institutes of Health (GMO31332) (R.H.G.), the Arnold and Mabel Beckman Foundation (T.P.M.), and the National Science Foundation (T.S.A.) for financial support. The authors are grateful to Dr. William J. Wolf for helpful comments. The authors declare no conflict of interest.

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Accepted Version - 26ae145b41647c1dcd63071a32cc87b58b8de0a1d20b187e6d17da4837f7b0ce.pdf


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