title: Iridium-catalyzed regioselective and enantioselective allylation of trimethylsiloxyfuran.
abstract: We report the regio- and enantioselective allylation of an ester enolate, trimethylsiloxyfuran. This enolate reacts at the 3-position with linear aromatic allylic carbonates or aliphatic allylic benzoates to form the branched substitution products in the presence of a metallacyclic iridium catalyst. This process provides access to synthetically important 3-substituted butenolides in enantioenriched form. Stoichiometric reactions of the allyliridium intermediate suggest that the trimethylsiloxyfuran is activated by the carboxylate leaving group.
authors.affiliation: Department of Chemistry, University of California, Berkeley, California 94720, USA.
authors.forename: Wenyong
authors.initials: W
authors.lastname: Chen
authors.forename: John F
authors.initials: JF
authors.lastname: Hartwig
mesh_terms: D002384:Catalysis; D005663:Furans / Q000737:chemistry*; D007495:Iridium / Q000737:chemistry*; D013237:Stereoisomerism; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
chemical_list: D005663:Furans; D014297:Trimethylsilyl Compounds; D007495:Iridium