title: Palladium-catalyzed asymmetric allylic alkylation of 2-acylimidazoles as ester enolate equivalents.
abstract: A broad range of highly enantioenriched 2-acylimidazoles are synthesized by palladium-catalyzed decarboxylative asymmetric allylic alkylation (DAAA) of 2-imidazolo-substituted enol carbonates. The enantioenriched 2-acylimidazole products can easily be converted to the corresponding carboxylic acid, ester, amide, and ketone derivatives with complete retention of the enantiopurity. The synthetic utility of this new method is demonstrated in the short, efficient synthesis of cetiedil.
authors.affiliation: Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA. bmtrost@stanford.edu
authors.forename: Barry M
authors.initials: BM
authors.lastname: Trost
authors.forename: Konrad
authors.initials: K
authors.lastname: Lehr
authors.forename: David J
authors.initials: DJ
authors.lastname: Michaelis
authors.forename: Jiayi
authors.initials: J
authors.lastname: Xu
authors.forename: Andreas K
authors.initials: AK
authors.lastname: Buckl
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D000478:Alkylation; D002264:Carboxylic Acids / Q000737:chemistry; D002384:Catalysis; D007093:Imidazoles / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*
chemical_list: D000475:Alkenes; D002264:Carboxylic Acids; D007093:Imidazoles; D007659:Ketones; D010165:Palladium