title: Highly enantioselective construction of spiro[4H-pyran-3,3'-oxindoles] through a domino Knoevenagel/Michael/cyclization sequence catalyzed by cupreine.
abstract: The first enantioselective organocatalytic two- and three-component reactions via a domino Knoevenagel/Michael/cyclization sequence with cupreine as catalyst have been developed. A wide range of optically active spiro[4H-pyran-3,3'-oxindoles] were obtained in excellent yields (up to 99%) with good to excellent enantioselectivities (up to 97%) from simple and readily available starting materials under mild reaction conditions. These heterocyclic spirooxindoles will provide promising candidates for chemical biology and drug discovery.
authors.affiliation: Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China.
authors.forename: Wen-Bing
authors.initials: WB
authors.lastname: Chen
authors.forename: Zhi-Jun
authors.initials: ZJ
authors.lastname: Wu
authors.forename: Qing-Lan
authors.initials: QL
authors.lastname: Pei
authors.forename: Lin-Feng
authors.initials: LF
authors.lastname: Cun
authors.forename: Xiao-Mei
authors.initials: XM
authors.lastname: Zhang
authors.forename: Wei-Cheng
authors.initials: WC
authors.lastname: Yuan
mesh_terms: D002384:Catalysis; D003500:Cyclization; D007211:Indoles / Q000737:chemistry*; D000078183:Oxindoles; D011804:Quinolines / Q000737:chemistry*; D013141:Spiro Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D007211:Indoles; D000078183:Oxindoles; D011804:Quinolines; D013141:Spiro Compounds; C022960:2-oxindole; C552577:cupreine