title: Bicyclic guanidinium-catalyzed enantioselective phase-transfer alkylation: direct access to pyrroloindolines and furoindolines.
abstract: Highly enantioselective phase-transfer alkylation of 3-substituted-2-oxindoles with activated bromomethanes is disclosed with a broad substrate scope by using bicyclic guanidinium as a catalyst and a Lewis acid as the co-catalyst. The alkylation adducts are versatile intermediates to accomplish the syntheses of pyrroloindolines and furoindolines.
authors.affiliation: Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University, Kaifeng, Henan 475004, People's Republic of China. chmjzy@henu.edu.cn.
authors.forename: Wenchao
authors.initials: W
authors.lastname: Chen
authors.forename: Wenguo
authors.initials: W
authors.lastname: Yang
authors.forename: Lin
authors.initials: L
authors.lastname: Yan
authors.forename: Choon-Hong
authors.initials: CH
authors.lastname: Tan
authors.forename: Zhiyong
authors.initials: Z
authors.lastname: Jiang
mesh_terms: D000478:Alkylation; D001643:Bridged Bicyclo Compounds / Q000737:chemistry*; D002384:Catalysis; D019791:Guanidine / Q000737:chemistry*; D006842:Hydrocarbons, Brominated / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D000078183:Oxindoles; D044367:Phase Transition; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001643:Bridged Bicyclo Compounds; D006842:Hydrocarbons, Brominated; D007211:Indoles; D009942:Organometallic Compounds; D000078183:Oxindoles; D011758:Pyrroles; C022960:2-oxindole; C005218:methyl bromide; D019791:Guanidine