Journal
ORGANIC LETTERS
Volume 2, Issue 14, Pages 2145-2147Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol006059s
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[GRAPHICS] 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.
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