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Stereoretentive Olefin Metathesis: An Avenue to Kinetic Selectivity
Author(s) -
Montgomery T. Patrick,
Ahmed Tonia S.,
Grubbs Robert H.
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201704686
Subject(s) - olefin metathesis , olefin fiber , metathesis , catalysis , acyclic diene metathesis , salt metathesis reaction , selectivity , chemistry , combinatorial chemistry , organic chemistry , polymerization , polymer
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.