[reaction: see text] Macrocyclic ring-closing olefin metathesis using ruthenium catalyst 3 was performed to produce a 14-membered lactone. The E/Z ratio of lactone was high regardless of the R group (auxiliary) or the initial alkene stereochemistry. A kinetic study demonstrates that the high E/Z ratio is due to secondary metathesis reactions that isomerize the product to the thermodynamic E/Z ratio.
Communication
Ruthenium Olefin Metathesis Catalysts for the Ethenolysis of Renewable FeedstocksRuthenium olefin metathesis catalysts have been evaluated for the ethenolysis of methyl oleate, a natural seed oil derivative, to produce useful terminal olefins. Several N-heterocyclic carbene-based ruthenium catalysts demonstrate good activity and selectivity for the formation of terminal olefins. In particular, catalysts (10) and (21) achieved higher TONs (A20 000).
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