Synthesis of chiral β-aminophosphonates via Rh-catalyzed asymmetric hydrogenation of β-amido-vinylphosphonates

被引：29
|
作者：
Kadyrov, Renat [1 ,2 ]
Holz, Jens
Schaeffner, Benjamin
Zayas, Odalys [3 ]
Almena, Juan [1 ]
Boerner, Armin [1 ,2 ]
机构：
[1] Univ Rostock, Leibniz Inst Katalyse, D-18059 Rostock, Germany
[2] Evonik Ind, D-63457 Hanau, Germany
[3] Univ Rostock, Inst Chem, D-18059 Rostock, Germany
来源：
TETRAHEDRON-ASYMMETRY | 2008年 / 19卷 / 10期
关键词：
D O I：
10.1016/j.tetasy.2008.04.019
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The Rh-catalyzed asymmetric hydrogenation of prochiral beta-N-acetylamino-vinylphosphoniites allows the preparation of chiral beta-N-acetylamino-phosphonates with excellent yields (up to 100%) and. high enantioselectivities (up to 92% ee). The reaction is strongly dependent on the chiral bidentate phosphorus ligand and the solvent employed. In several cases an inversion of the induced chirality was noted by using the corresponding E- or Z-isomeric substrates. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1189 / 1192
页数：4
相关论文
共 50 条
  • [41] Enantioselective synthesis of optically active alkylphosphonates via Rh-catalyzed asymmetric hydrogenation of β-substituted α,β-unsaturated phosphonates
    Duan, Zheng-chao
    Wang, Lian-zhi
    Song, Xin-jian
    Hu, Xiang-ping
    Zheng, Zhuo
    TETRAHEDRON-ASYMMETRY, 2012, 23 (6-7) : 508 - 514
  • [42] New ionic phosphite ligands: synthesis and application in asymmetric Rh-catalyzed hydrogenation
    S. E. Lyubimov
    P. V. Petrovskii
    V. A. Davankov
    Russian Chemical Bulletin, 2009, 58 : 528 - 531
  • [43] Rh-catalyzed asymmetric hydrogenation of prochiral olefins with a dynamic library of chiral TROPOS phosphorus ligands
    Monti, C
    Gennari, C
    Piarulli, U
    de Vries, JG
    de Vries, AHM
    Lefort, L
    CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (22) : 6701 - 6717
  • [44] Facile access to chiral 4-substituted chromanes through Rh-catalyzed asymmetric hydrogenation
    Lin Tao
    Qingyang Zhao
    Xumu Zhang
    Xiu-Qin Dong
    Chinese Chemical Letters, 2020, 31 (07) : 1859 - 1862
  • [45] Mixtures of chiral and achiral monodentate ligands in asymmetric Rh-catalyzed olefin hydrogenation: reversal of enantioselectivity
    Reetz, MT
    Mehler, G
    TETRAHEDRON LETTERS, 2003, 44 (24) : 4593 - 4596
  • [46] Synthesis of Proline Analogues via Rh-Catalyzed Asymmetric Conjugate Addition
    Edelstein, Emma K.
    Rankic, Danica A.
    Dudley, Caroline C.
    McMinn, Spencer E.
    Adpressa, Donovon A.
    ACS CATALYSIS, 2021, 11 (02) : 743 - 749
  • [47] Supramolecular chiral dendritic monophosphites assembled by hydrogen bonding and their use in the Rh-catalyzed asymmetric hydrogenation
    Li, Yong
    He, Yan-Mei
    Li, Zhi-Wei
    Zhang, Feng
    Fan, Qing-Hua
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (09) : 1890 - 1895
  • [48] P-Chirogenic Diphosphazanes with Axially Chiral Substituents and Their Use in Rh-Catalyzed Asymmetric Hydrogenation
    Moritz, Jan-Ole
    Chakrabortty, Soumyadeep
    Mueller, Bernd H.
    Spannenberg, Anke
    Kamer, Paul C. J.
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (22): : 14537 - 14544
  • [49] Chiral carborane-derived thiophosphites: A new generation of ligands for Rh-catalyzed asymmetric hydrogenation
    Lyubimov, Sergey E.
    Davankov, Vadim A.
    Petrovskii, Pavel V.
    Hey-Hawkins, Evamarie
    Tyutyunov, Andrey A.
    Rys, Evgeny G.
    Kalinin, Valery N.
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2008, 693 (25) : 3689 - 3691
  • [50] Facile access to chiral 4-substituted chromanes through Rh-catalyzed asymmetric hydrogenation
    Tao, Lin
    Zhao, Qingyang
    Zhang, Xumu
    Dong, Xiu-Qin
    CHINESE CHEMICAL LETTERS, 2020, 31 (07) : 1859 - 1862
12345