Following our initial report of ruthenium metathesis catalysts with a chelating NHC that preferentially form the thermodynamically disfavored Z-isomer in cross metathesis reactions, much research has been performed attempting to find related analogs that have increased activity, stability, and also exhibit such high Z-selectivity. The decomposition pathways of such species have been elucidated and helps explain observed olefin migration of various substrates. Novel catalysts have also been developed that replace the N-adamantyl group with similar analogs and also exhibit high Z-selectivity. Finally, an improved Z-selective catalyst has been used to synthesize a number of Lepidopteran insect pheromones in one step that were previously inaccessible by olefin metathesis.

Z-selective ruthenium-based olefin metathesis: Catalyst development and application to the synthesis of insect pheromones

243rd National Meeting (2012)

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