Asymmetric hydrogenation of α-keto phosphonates with chiral phosphine-phosphoramidite ligands

被引:10
作者
Li, Qing [1 ,2 ]
Hou, Chuan-Jin [1 ,2 ]
Liu, Yan-Jun [1 ]
Yang, Rui-Feng [1 ]
Hu, Xiang-Ping [2 ]
机构
[1] Dalian Polytech Univ, Sch Light Ind & Chem Engn, Dalian 116034, Peoples R China
[2] Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China
基金
中国国家自然科学基金;
关键词
CATALYZED ENANTIOSELECTIVE HYDROGENATION; HYDROXY PHOSPHONATES; BETA-KETOESTERS; AL(SALALEN) COMPLEX; DIPHOSPHINE LIGANDS; KINETIC RESOLUTION; N-ARYLIMINES; HYDROPHOSPHONYLATION; ALDEHYDES; HYDROXYPHOSPHONATES;
D O I
10.1016/j.tetasy.2015.05.007
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Rh-catalyzed asymmetric hydrogenation of challenging alpha-keto phosphonates has been developed. With a new chiral phosphine-phosphoramidite ligand, a wide range of alpha-keto phosphonates were hydrogenated to afford the corresponding (R)-alpha-hydroxy phosphonates with moderate to good enantioselectivities (up to 87% ee). (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码:617 / 622
页数:6
相关论文
共 73 条
  • [1] [Anonymous], 1949, Advertising in Television'
  • [2] Catalytic asymmetric synthesis of alpha-hydroxy phosphonates using the Al-Li-BINOL complex
    Arai, T
    Bougauchi, M
    Sasai, H
    Shibasaki, M
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (09) : 2926 - 2927
  • [3] Hybrid bidentate phosphoramidite ligands in asymmetric catalysis
    Boeda, Fabien
    Beneyton, Thomas
    Crevisy, Christophe
    [J]. MINI-REVIEWS IN ORGANIC CHEMISTRY, 2008, 5 (02) : 96 - 127
  • [4] Diametric Stereocontrol in Dynamic Catalytic Reduction of Racemic Acyl Phosphonates: Divergence from α-Keto Ester Congeners
    Corbett, Michael T.
    Johnson, Jeffrey S.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (02) : 594 - 597
  • [5] Synthesis and molecular modeling studies of SYNPHOS®, a new, efficient diphosphane ligand for ruthenium-catalyzed asymmetric hydrogenation
    de Paule, SD
    Jeulin, S
    Ratovelomanana-Vidal, V
    Genêt, JP
    Champion, N
    Dellis, P
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (10) : 1931 - 1941
  • [6] BINOL-derived phosphoramidites in asymmetric hydrogenation: can the presence of a functionality in the amino group influence the catalytic outcome?
    Eberhardt, Luc
    Armspach, Dominique
    Harrowfield, Jack
    Matt, Dominique
    [J]. CHEMICAL SOCIETY REVIEWS, 2008, 37 (04) : 839 - 864
  • [7] Enantioselective hydrogenation of α-ketoesters over alkaloid-modified platinum nanowires
    Erathodiyil, Nandanan
    Gu, Hongwei
    Shao, Huilin
    Jiang, Jiang
    Ying, Jackie Y.
    [J]. GREEN CHEMISTRY, 2011, 13 (11) : 3070 - 3074
  • [8] Asymmetric Hydrogenation of α-Keto Phosphonates with Chiral Palladium Catalysts
    Goulioukina, Nataliya S.
    Bondarenko, Grigorii N.
    Bogdanov, Alexei V.
    Gavrilov, Konstantin N.
    Beletskaya, Irina P.
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (04) : 510 - 515
  • [9] Gröger H, 2000, CHEM-EUR J, V6, P943
  • [10] Hilderbrand R. L., 1983, The Role of Phosphonates in Living Systems