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Olefin Metathesis Involving Ruthenium Enoic Carbene Complexes

Choi, Tae-Lim and Lee, Choon Woo and Chatterjee, Arnab K. and Grubbs, Robert H. (2001) Olefin Metathesis Involving Ruthenium Enoic Carbene Complexes. Journal of the American Chemical Society, 123 (42). pp. 10417-10418. ISSN 0002-7863. https://resolver.caltech.edu/CaltechAUTHORS:20170411-114619011

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Abstract

Olefin metathesis has become a valuable reaction in organic synthesis, as has been demonstrated by its frequent use as the key bond constructions for total syntheses of many natural products. With the recent discovery of highly active catalyst 1, trisubstituted and functionalized alkenes have been synthesized efficiently by cross-metathesis (CM), further expanding the substrate scope for this reaction. With these successes in hand, unprecedented metathesis reactions were explored. There have been no previous reports of the dimerization of α,β-unsaturated carbonyl compounds by a metathesis mechanism. Molybdenum- and tungsten-based catalysts form metallocyclobutane with acrylates, but they are inactive due to carbonyl oxygen chelation. Our group reported the synthesis of ester carbene 4 by a nonmetathesis route and showed that 4 was extremely reactive. In fact, ester carbene 4 was the first carbene to ring-open cyclohexene but did not react in a catalytic fashion.4 The nontrivial synthesis, lack of stability, and the ineffective catalytic activity of ester carbene 4 has limited its uses in organic synthesis.


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http://dx.doi.org/10.1021/ja016386aDOIArticle
http://pubs.acs.org/doi/full/10.1021/ja016386aPublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/ja016386aRelated ItemSupporting Information
ORCID:
AuthorORCID
Grubbs, Robert H.0000-0002-0057-7817
Additional Information:© 2001 American Chemical Society. Received 11 June 2001. Published online 26 September 2001. Published in print 1 October 2001. We thank the NIH for generous support of this research, and Dr. M. Scholl, J. P. Morgan, Dr. S. D. Goldberg, Dr. F. D. Toste, Dr. M. S. Sanford and C. Morrill for helpful discussions.
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Issue or Number:42
Record Number:CaltechAUTHORS:20170411-114619011
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170411-114619011
Official Citation:Olefin Metathesis Involving Ruthenium Enoic Carbene Complexes Tae-Lim Choi, Choon Woo Lee, Arnab K. Chatterjee, and Robert H. Grubbs Journal of the American Chemical Society 2001 123 (42), 10417-10418 DOI: 10.1021/ja016386a
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:76512
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:11 Apr 2017 19:48
Last Modified:03 Oct 2019 17:02

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