title: Catalytic Asymmetric Conjugate Addition and Sulfenylation of Diarylthiazolidin-2,4-diones.
abstract: This work reports the first application of diarylthiazolidin-2,4-diones as nucleophiles in asymmetric catalysis. By utilizing chiral amino acid-based (thio)urea-tertiary amines as the catalysts, we successively established asymmetric conjugate addition to nitroolefins and sulfenylation to N-(sulfanyl)-succinimides of diarylthiazolidin-2,4-diones. Two series of biologically important 5-aryl-5-substituted thiazolidin-2,4-diones were obtained with high enantio- and diastereoselectivities (up to >99% ee and >19:1 dr). The enantioenriched adducts were found to show satisfactory anticancer activities against three different cancer cell lines using the MTT assay. All of these successes depended on the development of a general and expedient synthetic strategy to provide diverse 5H-thiazolidin-2,4-diones.
authors.affiliation: Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University , Kaifeng, Henan 475004, P.R. China.
authors.forename: Lihui
authors.initials: L
authors.lastname: Jiao
authors.affiliation: Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University , Kaifeng, Henan 475004, P.R. China.
authors.forename: Liwei
authors.initials: L
authors.lastname: Bu
authors.affiliation: Division of Chemistry and Biological Chemistry, Nanyang Technological University , 21 Nanyang Link, 637371 Singapore.
authors.forename: Xinyi
authors.initials: X
authors.lastname: Ye
authors.affiliation: Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University , Kaifeng, Henan 475004, P.R. China.
authors.forename: Xiaowei
authors.initials: X
authors.lastname: Zhao
authors.affiliation: Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University , Kaifeng, Henan 475004, P.R. China.
authors.forename: Zhiyong
authors.initials: Z
authors.lastname: Jiang