title: Regiospecific Hydration of N-(Diphenylphosphinoyl)propargyl Amines: Synthesis of β-Amino Ketones by Au(III) Catalysis.
abstract: A Au(III)-catalyzed regiospecific hydration of N-(diphenylphosphinoyl)propargyl amines has been developed to produce various β-amino ketones. These reactions are conducted in the presence of NaAuCl4·2H2O (10 mol %) in a mixed solvent of EtOH/H2O/CH2Cl2 (4:1:1) at room temperature to give the products in 45-71% yield. The high enantiomeric purity of a chiral N-(diphenylphosphinoyl)propargyl amine (85% ee) is maintained after hydration, which makes this method useful for the asymmetric synthesis of chiral β-amino ketones. Reduction of a β-amino ketone product with Zn(BH4)2 gives a 1,3-amino alcohol with modest diastereoselectivity.
authors.affiliation: Department of Chemistry, University of Virginia , Charlottesville, Virginia 22904-4319, United States.
authors.forename: Jun
authors.initials: J
authors.lastname: Ying
authors.affiliation: Department of Chemistry, University of Virginia , Charlottesville, Virginia 22904-4319, United States.
authors.forename: Lin
authors.initials: L
authors.lastname: Pu