title: Iridium-Catalyzed Asymmetric Hydrogenation of Racemic β-Keto Lactams via Dynamic Kinetic Resolution.
abstract: A highly efficient Ir-catalyzed asymmetric hydrogenation of racemic β-keto lactams via dynamic kinetic resolution (DKR) for the synthesis of optically active β-hydroxyl lactams has been described. With the Ir-SpiroSAP catalyst, a series of racemic β-keto lactams including β-keto γ-, δ-, and ε-lactams were hydrogenated to chiral β-hydroxy lactams in high yields (87-99%) with excellent enantio- and diastereoselectivity (83-99.9% ee, syn/anti: 97:3->99:1) at low catalyst loading under mild reaction conditions. This efficient method has been successfully applied in the synthesis of the chiral intermediate of fluoroquinolone antibiotic premafloxacine.
authors.affiliation: State Key Laboratory and Institute of Elemento-organic Chemistry, Nankai University , Tianjin 300071, China.
authors.forename: Deng-Hui
authors.initials: DH
authors.lastname: Bao
authors.affiliation: State Key Laboratory and Institute of Elemento-organic Chemistry, Nankai University , Tianjin 300071, China.
authors.forename: Xue-Song
authors.initials: XS
authors.lastname: Gu
authors.affiliation: State Key Laboratory and Institute of Elemento-organic Chemistry, Nankai University , Tianjin 300071, China.
authors.forename: Jian-Hua
authors.identifier: 0000-0003-3907-2530
authors.initials: JH
authors.lastname: Xie
authors.affiliation: State Key Laboratory and Institute of Elemento-organic Chemistry, Nankai University , Tianjin 300071, China.|Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University , Tianjin 300071, China.
authors.forename: Qi-Lin
authors.initials: QL
authors.lastname: Zhou
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis; D002384:Catalysis; D015195:Drug Design; D024841:Fluoroquinolones / Q000138:chemical synthesis; D006865:Hydrogenation; D007495:Iridium / Q000737:chemistry*; D007700:Kinetics; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis; D013237:Stereoisomerism; D047090:beta-Lactams / Q000737:chemistry*
chemical_list: D000900:Anti-Bacterial Agents; D024841:Fluoroquinolones; D011758:Pyrroles; D047090:beta-Lactams; D007495:Iridium; C105016:premafloxacin