title: Rhodium-catalyzed enantioselective addition of organoaluminum reagents to N-tosyl ketimines.
abstract: Rhodium(I)/Binap complexes catalyze highly enantioselective additions of methyl- and arylaluminum reagents to cyclic α,β-unsaturated N-tosyl ketimines. Depending on the solvent and substituents at the ring, the reaction occurs either in a 1,2-manner to deliver α-tertiary allylic amines or in a 1,4-manner to yield, after subsequent reduction, 3-substituted cycloalkyl amines. Well known in the case of the respective cycloalkenones, these first transformations of the aza-analogues enable the synthesis of amine structures of pharmaceutical and biochemical interest.
authors.affiliation: Fachbereich Chemie, Philipps-Universität Marburg , Hans-Meerwein-Straße, 35032 Marburg, Germany.
authors.forename: Sebastian
authors.initials: S
authors.lastname: Hirner
authors.forename: Andreas
authors.initials: A
authors.lastname: Kolb
authors.forename: Johannes
authors.initials: J
authors.lastname: Westmeier
authors.forename: Sandra
authors.initials: S
authors.lastname: Gebhardt
authors.forename: Stephen
authors.initials: S
authors.lastname: Middel
authors.forename: Klaus
authors.initials: K
authors.lastname: Harms
authors.forename: Paultheo
authors.initials: P
authors.lastname: von Zezschwitz
mesh_terms: D000535:Aluminum / Q000737:chemistry*; D002384:Catalysis; D056831:Coordination Complexes / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D007202:Indicators and Reagents / Q000737:chemistry*; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry*; D009570:Nitriles / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D056831:Coordination Complexes; D007097:Imines; D007202:Indicators and Reagents; D009281:Naphthalenes; D009570:Nitriles; C542835:ketimine; D000535:Aluminum; D012238:Rhodium