Stereoselectivity of Macrocyclic Ring-Closing Olefin Metathesis
- 17 June 2000
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 2 (14) , 2145-2147
- https://doi.org/10.1021/ol006059s
Abstract
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.Keywords
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