title: Hydrogen-Bonding Network Promoted [3+2] Cycloaddition: Asymmetric Catalytic Construction of Spiro-pseudoindoxyl Derivatives.
abstract: The enantioselective construction of a spirocyclic quaternary stereogenic carbon center at the C2 position of indole has long been an elusive problem in organic synthesis. Herein, by employing a rationally designed hydrogen-bonding network activation strategy, for the first time, 2,2'-pyrrolidinyl-spirooxindole, which is a valuable and prevalent indole alkaloid scaffold, was directly obtained through a catalytic asymmetric [3+2] cycloaddition reaction with high yields and excellent stereoselectivities.
authors.affiliation: State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, 730000, China.
authors.forename: Liang-Jie
authors.initials: LJ
authors.lastname: Zhang
authors.affiliation: School of Chemistry and Chemical Engineering, Shandong University, Jinan, 250100, China.
authors.forename: Yao
authors.initials: Y
authors.lastname: Wang
authors.affiliation: State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, 730000, China.
authors.forename: Xiu-Qin
authors.initials: XQ
authors.lastname: Hu
authors.affiliation: State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, 730000, China. xupf@lzu.edu.cn.
authors.forename: Peng-Fei
authors.initials: PF
authors.lastname: Xu
mesh_terms: D002384:Catalysis; D061565:Cycloaddition Reaction; D006860:Hydrogen Bonding; D007211:Indoles / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D007211:Indoles
keywords: [3+2] cycloaddition; azomethine ylides; hydrogen bonding; quaternary carbons; spiro-pseudoindoxyl