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Formation of Macrocycles via Ring-Closing Olefin Metathesis

Lee, Choon Woo and Grubbs, Robert H. (2001) Formation of Macrocycles via Ring-Closing Olefin Metathesis. Journal of Organic Chemistry, 66 (21). pp. 7155-7158. ISSN 0022-3263. https://resolver.caltech.edu/CaltechAUTHORS:20170404-103422409

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Abstract

The enhanced metathesis activity of 1,3-dimesityl-4,5-dihydroimidazole-2-ylidene ruthenium carbene catalyst 3 significantly increases the feasibility of synthesizing macrocyclic compounds. Catalyst 3 exhibits sufficient activity in RCM to dimerize α,β-unsaturated ester substrates and afford the corresponding head-to-tail (E,E)-dimeric (and trimeric) macrocycles. The dimerization appears to be under thermodynamic control with the product mixture dependent not only on the electronic and steric nature of the substrate but also on concentration.


Item Type:Article
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http://dx.doi.org/10.1021/jo0158480DOIArticle
http://pubs.acs.org/doi/abs/10.1021/jo0158480PublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/jo0158480PublisherSupporting Information
ORCID:
AuthorORCID
Grubbs, Robert H.0000-0002-0057-7817
Additional Information:© 2001 American Chemical Society. Received June 18, 2001; Publication Date (Web): September 15, 2001. Support has been generously provided by the National Institutes of Health. John P. Morgan, Christopher W. Bielawski, Arnab K. Chatterjee, and Tae-Lim Choi are also acknowledged for helpful discussions.
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NIHUNSPECIFIED
Issue or Number:21
Record Number:CaltechAUTHORS:20170404-103422409
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170404-103422409
Official Citation:Formation of Macrocycles via Ring-Closing Olefin Metathesis Choon Woo Lee and Robert H. Grubbs The Journal of Organic Chemistry 2001 66 (21), 7155-7158 DOI: 10.1021/jo0158480
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:75690
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:04 Apr 2017 18:52
Last Modified:03 Oct 2019 16:52

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