title: Synthetic route to chiral indolines via ring-opening/C-N cyclization of activated 2-haloarylaziridines.
abstract: A practical approach for the synthesis of 3-substituted indolines via regio- and stereoselective SN2-type ring-opening of 2-(2-halophenyl)-N-tosylaziridines with heteroatomic nucleophiles (O, N, and S) followed by palladium-catalyzed intramolecular C-N cyclization is reported in excellent yields (up to >99%) and enantiomeric excess (ee 99%).
authors.affiliation: Department of Chemistry, Indian Institute of Technology, Kanpur 208016, India. mkghorai@iitk.ac.in
authors.forename: Manas K
authors.initials: MK
authors.lastname: Ghorai
authors.forename: Y
authors.initials: Y
authors.lastname: Nanaji
mesh_terms: D001388:Aziridines / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D001388:Aziridines; D006846:Hydrocarbons, Halogenated; D007211:Indoles; C057812:indoline