title: Asymmetric Friedel-Crafts reaction of 4,7-dihydroindoles with nitroolefins by chiral Brønsted acids under low catalyst loading.
abstract: Slowly does it! By adding the substrate by a syringe pump, a highly efficient Friedel-Crafts reaction of 4,7-dihydroindoles with nitroolefins was realized with 0.5 mol % of a chiral phosphoric acid. The Friedel-Crafts alkylation, together with a subsequent oxidation of the product, led to 2-substituted indoles in excellent enantiomeric excesses, which can be easily transformed to enantioenriched tetrahydro-gamma-carbolines.
authors.affiliation: State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 54 Fenglin Lu, Shanghai, China.
authors.forename: Yi-Fei
authors.initials: YF
authors.lastname: Sheng
authors.forename: Gong-Qiang
authors.initials: GQ
authors.lastname: Li
authors.forename: Qiang
authors.initials: Q
authors.lastname: Kang
authors.forename: An-Jiang
authors.initials: AJ
authors.lastname: Zhang
authors.forename: Shu-Li
authors.initials: SL
authors.lastname: You
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D007211:Indoles / Q000737:chemistry*; D010756:Phosphoric Acids / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D007211:Indoles; D010756:Phosphoric Acids; C030242:phosphoric acid