title: Highly enantioselective organocatalytic sulfenylation of 3-aryloxindoles.
abstract: An organocatalytic asymmetric sulfenylation of 3-aryloxindoles with N-(sulfanyl)succinimides has been developed by using commercially available (DHQD)(2)PHAL as catalyst. Various chiral 3-benzylthio-, alkylthio-, and arylthio-substituted oxindoles, containing 3,3-disubstituted quarternary carbon stereocenters, could be obtained in high enantioselectivities (85-97% ee). Furthermore, the opposite enantiomers of the sulfenylated products were readily accessible with equal excellent enantioselectivities (86-95% ee) by replacing the catalyst with (DHQ)(2)PHAL.
authors.affiliation: Institute of Chemical Biology, Henan University, Kaifeng, Henan, People's Republic of China 475004.
authors.forename: Zhiqiang
authors.initials: Z
authors.lastname: Han
authors.forename: Wenchao
authors.initials: W
authors.lastname: Chen
authors.forename: Sheng
authors.initials: S
authors.lastname: Dong
authors.forename: Caiyun
authors.initials: C
authors.lastname: Yang
authors.forename: Hongjun
authors.initials: H
authors.lastname: Liu
authors.forename: Yuanhuang
authors.initials: Y
authors.lastname: Pan
authors.forename: Lin
authors.initials: L
authors.lastname: Yan
authors.forename: Zhiyong
authors.initials: Z
authors.lastname: Jiang
mesh_terms: D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D006574:Heterocyclic Compounds, 2-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure; D000078183:Oxindoles; D013237:Stereoisomerism; D013388:Succinimides / Q000737:chemistry; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D006574:Heterocyclic Compounds, 2-Ring; D007211:Indoles; D000078183:Oxindoles; D013388:Succinimides; D013438:Sulfhydryl Compounds; C022960:2-oxindole