title: Lewis acid-catalyzed enantioselective hydroxylation reactions of oxindoles and beta-keto esters using DBFOX ligand.
abstract: The first catalytic enantioselective hydroxylation reaction of both 3-aryl and 3-alkyl-2-oxindoles using the DBFOX-Zn(II) complex, leading to pharmaceutically important chiral 3-hydroxy-2-oxindoles was described. The structure of oxidant was found to play an important role to increase the enantioselectivity. The methodology has successfully applied to the highly enantioselective hydroxylation of beta-keto esters using the DBFOX-Ni(II) complex.
authors.affiliation: Department of Applied Chemistry, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan.
authors.forename: Takehisa
authors.initials: T
authors.lastname: Ishimaru
authors.forename: Norio
authors.initials: N
authors.lastname: Shibata
authors.forename: Jun
authors.initials: J
authors.lastname: Nagai
authors.forename: Shuichi
authors.initials: S
authors.lastname: Nakamura
authors.forename: Takeshi
authors.initials: T
authors.lastname: Toru
authors.forename: Shuji
authors.initials: S
authors.lastname: Kanemasa
mesh_terms: D002384:Catalysis; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry; D006575:Heterocyclic Compounds, 3-Ring / Q000737:chemistry; D006900:Hydroxylation; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D008024:Ligands; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry; D010080:Oxazoles / Q000737:chemistry; D000078183:Oxindoles; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry*
chemical_list: D004952:Esters; D006575:Heterocyclic Compounds, 3-Ring; D007211:Indoles; D007659:Ketones; D008024:Ligands; D010080:Oxazoles; D000078183:Oxindoles; C022960:2-oxindole; D009532:Nickel; D015032:Zinc