Welcome to the new version of CaltechAUTHORS. Login is currently restricted to library staff. If you notice any issues, please email coda@library.caltech.edu
Published July 13, 2000 | public
Journal Article

Stereoselectivity of Macrocyclic Ring-Closing Olefin Metathesis


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.

Additional Information

© 2000 American Chemical Society. Received May 13, 2000. Publication Date (Web): June 17, 2000. Support has been generously provided by the National Institute of Health. C.W.L. acknowledges the Korea Science and Engineering Foundation (KOSEF) for a postdoctoral fellowship. The authors thank Christopher W. Bielawski, John P. Morgan, Dr. Michael Ulman, and Dr. Hyunjin Kim for useful discussions. Matthias Scholl and Melanie S. Sanford are acknowledged for the generous supply of catalyst 3.

Additional details

August 19, 2023
October 26, 2023