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Stereoselectivity of Macrocyclic Ring-Closing Olefin Metathesis

Lee, Choon Woo and Grubbs, Robert H. (2000) Stereoselectivity of Macrocyclic Ring-Closing Olefin Metathesis. Organic Letters, 2 (14). pp. 2145-2147. ISSN 1523-7060. https://resolver.caltech.edu/CaltechAUTHORS:20170807-160413253

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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.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1021/ol006059sDOIArticle
http://pubs.acs.org/doi/abs/10.1021/ol006059sPublisherArticle
ORCID:
AuthorORCID
Grubbs, Robert H.0000-0002-0057-7817
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.
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NIHUNSPECIFIED
Korea Science and Engineering FoundationUNSPECIFIED
Issue or Number:14
Record Number:CaltechAUTHORS:20170807-160413253
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170807-160413253
Official Citation:Stereoselectivity of Macrocyclic Ring-Closing Olefin Metathesis. Choon Woo Lee and Robert H. Grubbs Organic Letters 2000 2 (14), 2145-2147 DOI: 10.1021/ol006059s
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:79881
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:07 Aug 2017 23:08
Last Modified:03 Oct 2019 18:25

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