Enyne metathesis (enyne bond reorganization).

Enyne metathesis is a bond reorganization of an alkene and an alkyne to produce a 1,3-diene (eqs 1 and 2 in Scheme 1). It has been used in both intramolecular and intermolecular applications. Enyne metathesis bears a mechanistic kinship to alkene metathesis; however, it is less-studied than alkene metathesis. The enyne bond reorganization is atom economical and is driven by the enthalpic stability of the conjugated 1,3-diene produced. Stereoselection is often low in intermolecular cases but can be controlled in intramolecular cases. The enyne metathesis can be catalyzed by metal carbenes or “templated” by metal salts. Many of the same metal carbenes that catalyze alkene metathesis can be used to promote enyne metathesis.1 Steven T. Diver grew up in Salt Lake City and attended the University of Utah where he studied with Professor F. G. West as an undergraduate researcher. Diver went on to do his doctoral work with Professor Ed Vedejs at the University of WisconsinsMadison, studying nucleophilic catalysis promoted by phosphines. Diver conducted postdoctoral studies with Professor Stuart Schreiber at Harvard where he used alkene metathesis to make chemical dimerizers. Presumably this is where he got bitten by the metathesis bug. Diver began his independent work at the University at Buffalo−The State University of New York (SUNY−Buffalo) in 1997. Diver’s research group is interested in the application of enyne metathesis to challenging synthetic problems, mechanistic aspects of the enyne metathesis, and catalyst design employing unusual heterocyclic carbene ligands.