title: Pentanidium-catalyzed enantioselective α-hydroxylation of oxindoles using molecular oxygen.
abstract: Pentanidium-catalyzed α-hydroxylation of 3-substituted-2-oxindoles using molecular oxygen has been developed with good yields and enantioselectivities. This reaction does not require an additional reductant such as triethyl phosphite, which was typically added to reduce the peroxide intermediate. The reaction was demonstrated to consist of two-steps: an enantioselective formation of hydroperoxide oxindole and a kinetic resolution of the hydroperoxide oxindole via reduction with enolates generated from the oxindoles.
authors.affiliation: Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543.
authors.forename: Yuanyong
authors.initials: Y
authors.lastname: Yang
authors.forename: Farhana
authors.initials: F
authors.lastname: Moinodeen
authors.forename: Willy
authors.initials: W
authors.lastname: Chin
authors.forename: Ting
authors.initials: T
authors.lastname: Ma
authors.forename: Zhiyong
authors.initials: Z
authors.lastname: Jiang
authors.forename: Choon-Hong
authors.initials: CH
authors.lastname: Tan
mesh_terms: D002384:Catalysis; D006900:Hydroxylation; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure; D000078183:Oxindoles; D010100:Oxygen / Q000737:chemistry; D017905:Phosphites / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D007211:Indoles; D000078183:Oxindoles; D017905:Phosphites; C022960:2-oxindole; C018680:triethyl phosphite; D010100:Oxygen