title: Highly efficient enantioselective construction of bispirooxindoles containing three stereocenters through an organocatalytic cascade Michael-cyclization reaction.
abstract: Bispirooxindole derivatives containing three stereocenters, including two spiro quaternary centers, were synthesized in a high-yielding, atypically rapid, and stereocontrolled cascade Michael-cyclization reaction between methyleneindolinones and isothiocyanato oxindoles catalyzed by a bi- or multifunctional organocatalyst. Mild conditions were used to construct bispirooxindoles with excellent enantio- and diastereomeric purities within less than 1 min. Catalyst reconfiguration offered access to the opposite enantiomer. This exceptionally highly efficient procedure will allow diversity-oriented syntheses of this intriguing class of compounds with potential biological activities.
authors.affiliation: State Key Laboratory of Elemento-Organic Chemistry, Department of Chemistry, Nankai University, Tianjin 300071, PR China.
authors.forename: Hao
authors.initials: H
authors.lastname: Wu
authors.forename: Li-Li
authors.initials: LL
authors.lastname: Zhang
authors.forename: Zhi-Qing
authors.initials: ZQ
authors.lastname: Tian
authors.forename: Yao-Dong
authors.initials: YD
authors.lastname: Huang
authors.forename: Yong-Mei
authors.initials: YM
authors.lastname: Wang
mesh_terms: D002384:Catalysis; D003500:Cyclization; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D000078183:Oxindoles; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D007211:Indoles; D000078183:Oxindoles; D013141:Spiro Compounds; C022960:2-oxindole