title: Enantioselective functionalization of indoles and pyrroles via an in situ-formed spiro intermediate.
abstract: Herein we report a highly enantioselective synthesis of polycyclic indoles and pyrroles with up to 99% ee by an iridium catalyst system consisting of a commercially available iridium precursor and a readily accessible ligand. Investigation of the reaction mechanism led to the discovery of an unprecedented dearomatized spiro intermediate and its in situ migration phenomenon. The new reaction mode features switching of the substituent from the indole C-3 position to the C-2 position (from the C-2 position to the C-3 position in the case of pyrrole) without loss of the enantiomeric purity, providing a novel concept in designing the asymmetric construction of enantiopure polycyclic indoles and pyrroles.
authors.affiliation: State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry , Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China.
authors.forename: Chun-Xiang
authors.initials: CX
authors.lastname: Zhuo
authors.forename: Qing-Feng
authors.initials: QF
authors.lastname: Wu
authors.forename: Qiang
authors.initials: Q
authors.lastname: Zhao
authors.forename: Qing-Long
authors.initials: QL
authors.lastname: Xu
authors.forename: Shu-Li
authors.initials: SL
authors.lastname: You
mesh_terms: D002384:Catalysis; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D007495:Iridium / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D007211:Indoles; D009942:Organometallic Compounds; D011758:Pyrroles; D013141:Spiro Compounds; D007495:Iridium