Welcome to the new version of CaltechAUTHORS. Login is currently restricted to library staff. If you notice any issues, please email coda@library.caltech.edu
Published October 21, 2001 | Supplemental Material
Journal Article Open

Olefin Metathesis Involving Ruthenium Enoic Carbene Complexes


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.

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.

Attached Files

Supplemental Material - ja016386a_s1.pdf


Files (49.3 kB)
Name Size Download all
49.3 kB Preview Download

Additional details

August 19, 2023
October 25, 2023