title: Asymmetric substitution at the tetrasubstituted chiral carbon: catalytic ring-opening alkylation of racemic 2,2-disubstituted aziridines with 3-substituted oxindoles.
abstract: A highly diastereo- and enantioselective ring-opening alkylation of racemic 2,2-disubstituted aziridines with 3-substituted oxindoles is achieved under the catalysis of a chiral 1,2,3-triazolium salt. This reaction represents a hitherto unknown, catalytic stereoselective carbon-carbon bond formation through direct substitution at the tetrasubstituted chiral carbon.
authors.affiliation: Institute of Transformative Bio-Molecules (WPI-ITbM), and Department of Applied Chemistry, Graduate School of Engineering, Nagoya University , Nagoya, 464-8603, Japan.
authors.forename: Kohsuke
authors.initials: K
authors.lastname: Ohmatsu
authors.forename: Yuichiro
authors.initials: Y
authors.lastname: Ando
authors.forename: Takashi
authors.initials: T
authors.lastname: Ooi
mesh_terms: D000478:Alkylation; D001388:Aziridines / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D007211:Indoles / Q000737:chemistry*; D008958:Models, Molecular; D000078183:Oxindoles; D013237:Stereoisomerism
chemical_list: D001388:Aziridines; D007211:Indoles; D000078183:Oxindoles; C022960:2-oxindole; D002244:Carbon