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In summary, a catalytic platform for carbonyl-olefin meta-
thesis has been developed that utilizes simple organic catalysts
and classic pericyclic reactions. With the current procedure,
less-strained olefins such as norbornene or stilbene have not
been observed to undergo methathesis. However, the develop-
ment of catalysts that facilitate the cycloreversion step of this
mechanistic design is expected to enable the extension of this
process to a broader array of substrates. Such efforts are
currently underway in our laboratory.
(6) Brønsted acid promoted carbonyl-olefin metathesis: Schaik, H.-P.
v.; Vijn, R.-J.; Bickelhaupt, F. Angew. Chem., Int. Ed. 1994, 33, 1611−
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(7) Lewis acid promoted carbonyl-olefin metathesis reactions:
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Groot, A. d. Tetrahedron Lett. 2006, 47, 6715−6718. (c) Soicke, A.;
ASSOCIATED CONTENT
* Supporting Information
■
S
Experimental procedures and product characterization data.
This material is available free of charge via the Internet at
Slavov, N.; Neudorfl, J.-M.; Schmalz, H.-G. Synlett 2011, 2487−2490.
̈
(8) Bach, T. Synthesis 1998, 683−703.
(9) For selected examples of other catalytic double bond metathesis
reactions, see: (a) Cantrell, G. K.; Meyer, T. Y. Organometallics 1997,
16, 5381−5383. (b) Cantrell, G. K.; Meyer, T. Y. J. Am. Chem. Soc.
1998, 120, 8035−8042. (c) Bell, S. A.; Meyer, T. Y.; Geib, S. J. J. Am.
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(f) Campbell, T. W.; Monagle, J. J. J. Am. Chem. Soc. 1962, 84,
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Phosphorus, Sulfur, and Silcon 1993, 81, 37−48.
AUTHOR INFORMATION
Corresponding Author
■
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
Funding for this work was provided by the National Science
Foundation under CHE-0953259. T.H.L. is grateful for an
Alfred P. Sloan Research Fellowship and an Eli Lilly Grantee
Award. We thank Aaron Sattler and the Parkin group for X-ray
structure determination, and the National Science Foundation
(CHE-0619638) is thanked for acquisition of an X-ray
diffractometer.
(10) Katz, T. J.; McGinnis, J. J. Am. Chem. Soc. 1975, 97, 1592−1593.
(11) For reviews on 1,3-dipolar cycloreversions, see: (a) Bianchi, G.;
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D
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