title: Regiodivergent kinetic resolution of terminal and internal rac-aziridines with malonates under dinuclear Schiff base catalysis.
abstract: Regiodivergent parallel kinetic resolution of aziridines with malonates was achieved under dinuclear Schiff base catalysis. The regiodivergent reaction proceeded under catalyst-control irrespective of the substituents on the aziridines, and 2.5-10 mol % of a Y(OTf)3/La(OiPr)3/a dinucleating Schiff base = 1:1:1 mixture gave versatile γ-amino acid derivatives in 96 → >99.5% ee. Not only terminal but also internal racemic aziridines reacted smoothly under suitably combined Lewis acid/Brønsted base catalysis.
authors.affiliation: Graduate School of Pharmaceutical Sciences, the University of Tokyo , 7-3-1 Hongo Bunkyo-ku, Tokyo 113-0033, Japan.
authors.forename: Yingjie
authors.initials: Y
authors.lastname: Xu
authors.forename: Keiichi
authors.initials: K
authors.lastname: Kaneko
authors.forename: Motomu
authors.initials: M
authors.lastname: Kanai
authors.forename: Masakatsu
authors.initials: M
authors.lastname: Shibasaki
authors.forename: Shigeki
authors.initials: S
authors.lastname: Matsunaga
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D001388:Aziridines / Q000737:chemistry*; D002384:Catalysis; D007700:Kinetics; D008314:Malonates / Q000737:chemistry*; D008968:Molecular Conformation; D009942:Organometallic Compounds / Q000737:chemistry*; D012545:Schiff Bases / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D001388:Aziridines; D008314:Malonates; D009942:Organometallic Compounds; D012545:Schiff Bases