title: Ring opening/C-N cyclization of activated aziridines with carbon nucleophiles: highly diastereo- and enantioselective synthesis of tetrahydroquinolines.
abstract: A simple strategy for the synthesis of substituted tetrahydroquinolines through regio- and stereoselective ring opening of N-tosyl aziridines with carbon nucleophiles generated from 2-(bromoaryl)acetonitriles followed by palladium-catalyzed intramolecular C-N cyclization is reported in excellent yields (up to >99%) and stereoselectivity (ee and de up to >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
authors.forename: A K
authors.initials: AK
authors.lastname: Yadav
mesh_terms: D001388:Aziridines / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D003500:Cyclization; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry*; D011804:Quinolines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001388:Aziridines; D011804:Quinolines; D002244:Carbon; C542964:1,2,3,4-tetrahydroquinoline; D009584:Nitrogen