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 http://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.
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| 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. | ||||||||
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| Record Number: | CaltechAUTHORS:20100316-082743202 | ||||||||
| Persistent URL: | http://resolver.caltech.edu/CaltechAUTHORS:20100316-082743202 | ||||||||
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| 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: | 26 Dec 2012 11:50 |
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