title: Chiral counteranion synergistic organocatalysis under high temperature: efficient construction of optically pure spiro[cyclohexanone-oxindole] backbone.
abstract: The combination of a cinchona-based chiral primary amine and a BINOL-phosphoric acid has been demonstrated as a powerful and synergistic catalyst system for the double Michael addition of isatylidene malononitriles with α,β-unsaturated ketones, to provide the novel chiral spiro [cyclohexane-1,3'-indoline]-2',3-diones in high yields (88-99%) with excellent diastereo- and enantioselectivities (94:6-99:1 dr's, 95-99% ee's).
authors.affiliation: Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow (Suzhou) University, Suzhou 215123, PR China.
authors.forename: Yu-Bao
authors.initials: YB
authors.lastname: Lan
authors.forename: Hua
authors.initials: H
authors.lastname: Zhao
authors.forename: Zhao-Min
authors.initials: ZM
authors.lastname: Liu
authors.forename: Guo-Gui
authors.initials: GG
authors.lastname: Liu
authors.forename: Jing-Chao
authors.initials: JC
authors.lastname: Tao
authors.forename: Xing-Wang
authors.initials: XW
authors.lastname: Wang
mesh_terms: D000588:Amines / Q000737:chemistry; D002384:Catalysis; D002929:Cinchona / Q000737:chemistry; D003512:Cyclohexanones / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009284:Naphthols / Q000737:chemistry; D000078183:Oxindoles; D010756:Phosphoric Acids / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013696:Temperature
chemical_list: D000588:Amines; C406944:BINOL, naphthol; D003512:Cyclohexanones; D007211:Indoles; D009284:Naphthols; D000078183:Oxindoles; D010756:Phosphoric Acids; D013141:Spiro Compounds; C022960:2-oxindole; C036468:cyclohexanone; C030242:phosphoric acid