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Org Lett. 2000 Jul 13;2(14):2145-7.

Stereoselectivity of macrocyclic ring-closing olefin metathesis.

Author information

  • 1The Arnold and Mabel Beckman Laboratory of Chemical Synthesis, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, USA.

Erratum in

  • Org Lett 2000 Aug 10;1(16):2558.


[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.

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