title: Merging aerobic oxidation and enamine catalysis in the asymmetric α-amination of β-ketocarbonyls using N-hydroxycarbamates as nitrogen sources.
abstract: We describe herein an unprecedented asymmetric α-amination of β-ketocarbonyls under aerobic conditions. The process is enabled by a simple chiral primary amine through the coupling of a catalytic enamine ester intermediate and a nitrosocarbonyl (generated in situ) derived from N-hydroxycarbamate. The reaction features high chemoselectivity and excellent enantioselectivity for a broad range of substrates.
authors.affiliation: Beijing National Laboratory for Molecular Sciences (BNLMS), CAS Key Laboratory for Molecular Recognition and Function, Institute of Chemistry, The Chinese Academy of Sciences, Beijing, 100190 (China) http://luosz.iccas.ac.cn; Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, 300071 (China).
authors.forename: Changming
authors.initials: C
authors.lastname: Xu
authors.forename: Long
authors.initials: L
authors.lastname: Zhang
authors.forename: Sanzhong
authors.initials: S
authors.lastname: Luo
mesh_terms: D000586:Amination / Q000502:physiology*; D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000588:Amines; D009584:Nitrogen
keywords: aerobic oxidation; enamine catalysis; organocatalysis; α-amination; β-ketocarbonyls