title: Asymmetric decarboxylative allylation of oxindoles.
abstract: An asymmetric decarboxylative palladium-catalyzed allylation of alkyl- and aryl-substituted oxindoles has been developed, enabling the installation of an all-carbon quaternary chiral center at the oxindole 3-position in excellent yields and good to excellent enantioselectivity. An intriguing substrate-dependent reversal in stereoselectivity has been observed, whereby the size of the substituent determines the facial selectivity in the allylation step.
authors.affiliation: Department of Chemistry, University of York, Heslington, York YO10 5DD, UK.
authors.forename: Vilius
authors.initials: V
authors.lastname: Franckevičius
authors.forename: James D
authors.initials: JD
authors.lastname: Cuthbertson
authors.forename: Mark
authors.initials: M
authors.lastname: Pickworth
authors.forename: David S
authors.initials: DS
authors.lastname: Pugh
authors.forename: Richard J K
authors.initials: RJ
authors.lastname: Taylor
mesh_terms: D000498:Allyl Compounds / Q000138:chemical synthesis*; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure; D000078183:Oxindoles; D013237:Stereoisomerism
chemical_list: D000498:Allyl Compounds; D007211:Indoles; D000078183:Oxindoles; C022960:2-oxindole