Ruthenium-catalyzed decarboxylative allylation of nonstabilized ketone enolates.
[reaction: see text] Bipyridyl(pentamethylcyclopentadienyl)ruthenium chloride is an efficient catalyst for the formal [3,3] rearrangement of allyl beta-ketoesters. The mechanism of the transformation involves formation of pi-allyl ruthenium intermediates, which are selectively attacked at the more substituted allyl terminus by freely diffusing enolates. Decarboxylation of beta-ketocarboxylates allows generation of enolates under extremely mild conditions.
Burger
Erin C
EC
Department of Chemistry, University of Kansas, Lawrence, Kansas 66045, USA.
Tunge
Jon A
JA