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Low Catalyst Loadings in Olefin Metathesis: Synthesis of Nitrogen Heterocycles by Ring-Closing Metathesis

Kuhn, Kevin M. and Champagne, Timothy M. and Hong, Soon Hyeok and Wei, Wen-Hao and Nickel, Andrew and Lee, Choon Woo and Virgil, Scott C. and Grubbs, Robert H. and Pederson, Richard L. (2010) Low Catalyst Loadings in Olefin Metathesis: Synthesis of Nitrogen Heterocycles by Ring-Closing Metathesis. Organic Letters, 12 (5). pp. 984-987. ISSN 1523-7060. PMCID PMC3871858. https://resolver.caltech.edu/CaltechAUTHORS:20100316-082743202

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Abstract

A series of ruthenium catalysts have been screened under ring-closing metathesis (RCM) conditions to produce five-, six-, and seven-membered carbamate-protected cyclic amines. Many of these catalysts demonstrated excellent RCM activity and yields with as low as 500 ppm catalyst loadings. RCM of the five-membered carbamate series could be run neat, the six-membered carbamate series could be run at 1.0 M, and the seven-membered carbamate series worked best at 0.2−0.05 M.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ol9029808 DOIArticle
http://pubs.acs.org/doi/full/10.1021/ol9029808?cookieSet=1PublisherArticle
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3871858/PubMed CentralArticle
ORCID:
AuthorORCID
Hong, Soon Hyeok0000-0003-0605-9735
Grubbs, Robert H.0000-0002-0057-7817
Additional Information:© 2010 American Chemical Society. Received December 30, 2009. Publication Date (Web): February 8, 2010. We gratefully acknowledge financial support from the DOE (DE-FG02-08ER15933), the NIH (5RO1 GM31332), and the Gordon and Betty Moore Foundation. We thank Dr. Xiaohong Bei and Dr. Daryl Allen, Materia Inc., for helpful discussions.
Funders:
Funding AgencyGrant Number
Department of Energy (DOE)DE-FG02-08ER15933
NIH5RO1 GM31332
Gordon and Betty Moore FoundationUNSPECIFIED
Issue or Number:5
PubMed Central ID:PMC3871858
Record Number:CaltechAUTHORS:20100316-082743202
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20100316-082743202
Official Citation:Low Catalyst Loadings in Olefin Metathesis: Synthesis of Nitrogen Heterocycles by Ring-Closing Metathesis Kevin M. Kuhn, Timothy M. Champagne, Soon Hyeok Hong, Wen-Hao Wei, Andrew Nickel, Choon Woo Lee, Scott C. Virgil, Robert H. Grubbs, Richard L. Pederson Organic Letters 2010 12 (5), 984-987
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:17744
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:22 Mar 2010 03:11
Last Modified:03 Oct 2019 01:32

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