title: The Ti-BINOLate-catalyzed, enantioselective ring-opening of meso-aziridines with amines.
abstract: The titanium-BINOLate-catalyzed, highly enantioselective ring-opening reaction of meso-aziridines has been developed which furnishes trans-1,2-diamines in typically good yields and excellent enantioselectivities. N-Aryl aziridines attached to a 5- or 6-membered carbocyclic ring are among the best substrates for this process providing the products in up to >99% ee. The chiral catalyst is easily prepared in situ from commercially available components and does not require any laborious ligand synthesis. Structural investigations into the catalyst composition reveal an oligomeric structure of the active Ti-complex.
authors.affiliation: Institut für Organische Chemie, Universität Leipzig, Johannisallee 29, 04103 Leipzig, Germany.
authors.forename: Saravanan
authors.initials: S
authors.lastname: Peruncheralathan
authors.forename: Sandra
authors.initials: S
authors.lastname: Aurich
authors.forename: Henrik
authors.initials: H
authors.lastname: Teller
authors.forename: Christoph
authors.initials: C
authors.lastname: Schneider
mesh_terms: D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry*; D001388:Aziridines / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D009284:Naphthols / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D014025:Titanium / Q000737:chemistry*
chemical_list: D000588:Amines; D001388:Aziridines; C406944:BINOL, naphthol; D009284:Naphthols; D009942:Organometallic Compounds; D014025:Titanium