Further Information
Literature
Related Reactions
Olefin Metathesis
Ring Closing Metathesis
Ring Opening Metathesis
Cross Metathesis
The transalkylidenation of two terminal alkenes under release of ethene, catalyzed by ruthenium carbenoids (Grubbs Catalyst). Statistically, the reaction can lead to three possible pairs of geometric isomers, i.e. E/Z pairs for two homocouplings and the cross-coupling (R-CH=CH-R, R'-CH=CH-R', and R-CH=CH-R') - a total of 6 products.
The selectivity of this reaction is currently undergoing further study, but various examples exist in which two alkenes with different reactivity give the cross-coupled product with excellent yields and excellent selectivity.
Mechanism
Recent Literature
Regioselective Cross-Metathesis Reaction Induced by Steric Hindrance
S. BouzBouz, R. Simmons, J. Cossy, Org. Lett., 2004, 6, 3465-3467.
Selective Synthesis of (2Z,4E)-Dienyl Esters by Ene-Diene Cross
Metathesis
G. Moura-Letts, D. P. Curran, Org. Lett., 2007,
9, 5-8.
Advanced Fine-Tuning of Grubbs/Hoveyda Olefin Metathesis Catalysts: A
Further Step toward an Optimum Balance between Antinomic Properties
M. Bieniek, R. Bujok, M. Cabaj, N. Lugan, G. Lavigne, D. Arlt, K. Grela, J. Am. Chem. Soc., 2006,
128, 13652-13653.
A Good Bargain: An Inexpensive, Air-Stable Ruthenium Metathesis Catalyst
Derived from α-Asarone
K. Grela, M. Kim, Eur. J. Org. Chem., 2003,
963-966.
The facile preparation of alkenyl metathesis synthons
T. W. Baughman, J. C. Sworen, K. B. Wagener, Tetrahedron, 2004, 60, 10943-10948.
Ruthenium-Catalyzed Tandem Olefin Metathesis-Oxidations
A. A. Scholte, M. H. An, M. L. Snapper, Org. Lett., 2006, 8, 4759-4762.
Ruthenium-Catalyzed Tandem Cross-Metathesis/Wittig Olefination: Generation
of Conjugated Dienoic Esters from Terminal Olefins
R. P. Murelli, M. L. Snapper, Org. Lett., 2007,
9, 1749-1752.
Preparation of Aliphatic Ketones through a Ruthenium-Catalyzed Tandem
Cross-Metathesis/Allylic Alcohol Isomerization
D. Finnegan, B. A. Seigal, M. L. Snapper, Org. Lett., 2006, 8, 2603-2606.
Selected Articles
The Grubbs Reaction in Organic Synthesis
Enantioselective Total Synthesis of (+)-Amphidinolide T1
