Synthesis of a new class of conformationally rigid phosphino-oxazolines: Highly enantioselective ligands for Ir-catalyzed asymmetric hydrogenation

被引:83
|
作者
Liu, D [1 ]
Tang, WJ [1 ]
Zhang, X [1 ]
机构
[1] Penn State Univ, Dept Chem, University Pk, PA 16802 USA
关键词
D O I
10.1021/ol0362717
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new class of conformationally rigid phosphino-oxazoline ligands were synthesized from readily available enantiopure phenyl glycinol. Ir complexes with these ligands are air-stable and highly enantioselective catalysts for asymmetric hydrogenation of aryl alkenes and alpha,beta-unsaturated esters in up to 99% ee.
引用
收藏
页码:513 / 516
页数:4
相关论文
共 50 条
  • [21] Enantioselective Ir-Catalyzed Hydrogenation of Terminal Homoallyl Sulfones: Total Synthesis of (-)-Curcumene
    Bellido, Marina
    Riego-Mejias, Carlos
    Diaz-Moreno, Alejandro
    Verdaguer, Xavier
    Riera, Antoni
    ORGANIC LETTERS, 2023, 25 (09) : 1453 - 1457
  • [22] Asymmetric Ir-catalyzed hydrogenation of 1,5-benzodiazepinones using mixtures of ligands
    S. E. Lyubimov
    D. V. Ozolin
    V. A. Davankov
    Russian Chemical Bulletin, 2017, 66 : 1059 - 1061
  • [23] The Use of Phosphite-Type Ligands in the Ir-Catalyzed Asymmetric Hydrogenation of Heterocyclic Compounds
    Lyubimov, Sergey E.
    Ozolin, Dmitry V.
    Ivanov, Pavel Yu
    Melman, Artem
    Velezheva, Valeriya S.
    Davankov, Vadim A.
    CHIRALITY, 2014, 26 (01) : 56 - 60
  • [24] Ir-catalyzed Asymmetric Hydrogenation of α-Imino Esters with Chiral Ferrocenylphosphine-Phosphoramidite Ligands
    Hu, Xin-Hu
    Hu, Xiang-Ping
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (21) : 5063 - 5068
  • [25] Asymmetric Ir-catalyzed hydrogenation of 1,5-benzodiazepinones using mixtures of ligands
    Lyubimov, S. E.
    Ozolin, D. V.
    Davankov, V. A.
    RUSSIAN CHEMICAL BULLETIN, 2017, 66 (06) : 1059 - 1061
  • [26] Synthesis of new amidophosphite ligand and its application in Ir-catalyzed asymmetric hydrogenation of heterocyclic compounds
    Lyubimov, S. E.
    Ozolin, D. V.
    Pavlov, A. A.
    Fedorova, I. N.
    Velezheva, V. S.
    Davankov, V. A.
    RUSSIAN CHEMICAL BULLETIN, 2013, 62 (06) : 1405 - 1408
  • [27] Synthesis of new amidophosphite ligand and its application in Ir-catalyzed asymmetric hydrogenation of heterocyclic compounds
    S. E. Lyubimov
    D. V. Ozolin
    A. A. Pavlov
    I. N. Fedorova
    V. S. Velezheva
    V. A. Davankov
    Russian Chemical Bulletin, 2013, 62 : 1405 - 1408
  • [28] Tunable ferrocenyl diphosphine ligands for the Ir-catalyzed enantioselective hydrogenation of N-aryl imines
    Blaser, HU
    Buser, HP
    Häusel, R
    Jalett, HP
    Spindler, F
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 621 (1-2) : 34 - 38
  • [29] Chemoselective and Divergent Synthesis of Chlorohydrins and Oxaheterocycles via Ir-Catalyzed Asymmetric Hydrogenation
    Zong, Yan
    Zou, Xiaomei
    Song, Jingyuan
    Chen, Gen-Qiang
    Zhang, Xumu
    ORGANIC LETTERS, 2023, 25 (37) : 6875 - 6880