Asymmetric allylic alkylation of ketone enolates: an asymmetric Claisen surrogate.
[reaction: see text] The combination of catalytic palladium(0) and Trost ligand provides an effective catalyst for the rearrangement of allyl beta-ketoesters. The mechanism of the transformation involves formation of pi-allyl palladium intermediates which undergo enantioselective attack by ketone enolates. Decarboxylation of beta-ketocarboxylates allows regiospecific 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