Asymmetric Hydrophosphonylation of Aldehydes using a Cinchona-Diaminomethylenemalononitrile Organocatalyst

被引:41
作者
Hirashima, Shin-ichi [1 ]
Arai, Ryoga [1 ]
Nakashima, Kosuke [1 ]
Kawai, Nobuaki [1 ]
Kondo, Junko [1 ]
Koseki, Yuji [1 ]
Miura, Tsuyoshi [1 ]
机构
[1] Tokyo Univ Pharm & Life Sci, Hachioji, Tokyo 1920392, Japan
关键词
asymmetric reactions; diaminomethylenemalononitrile; hydrophosphonylation; organocatalysts; Pudovik reaction; ALPHA-HYDROXY PHOSPHONATES; CATALYZED ENANTIOSELECTIVE HYDROPHOSPHONYLATION; CONJUGATE ADDITION; AL(SALALEN) COMPLEX; THIOUREA; INHIBITORS; PHOSPHITE; DESIGN; IMINES; ACCESS;
D O I
10.1002/adsc.201500816
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
For the asymmetric hydrophosphonylation of aldehydes, an efficient organocatalytic approach with a diaminomethylenemalononitrilebased hydrogen-bonding donor catalyst is presented. The catalyst induces high yields and excellent enantioselectivities (up to 98% yield, 96% ee).
引用
收藏
页码:3863 / 3867
页数:5
相关论文
共 68 条
  • [1] Catalytic enantioselective Pudovik reaction of aldehydes and aldimines with tethered bis(8-quinolinato) (TBOx) aluminum complex
    Abell, Joshua P.
    Yamamoto, Hisashi
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (32) : 10521 - +
  • [2] Chiral Bronsted acid catalyzed enantioselective hydrophosphonylation of imines:: Asymmetric synthesis of α-amino phosphonates
    Akiyama, T
    Morita, H
    Itoh, J
    Fuchibe, K
    [J]. ORGANIC LETTERS, 2005, 7 (13) : 2583 - 2585
  • [3] Organocatalytic Asymmetric Synthesis of Organophosphorus Compounds
    Albrecht, Lukasz
    Albrecht, Anna
    Krawczyk, Henryk
    Jorgensen, Karl Anker
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (01) : 28 - 48
  • [4] Organocatalytic enantioselective hydrophosphonylation of aldehydes
    Alegre-Requena, Juan V.
    Marques-Lopez, Eugenia
    Sanz Miguel, Pablo J.
    Herrera, Raquel P.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (08) : 1258 - 1264
  • [5] Squaramides: Bridging from Molecular Recognition to Bifunctional Organocatalysis
    Aleman, Jose
    Parra, Alejandro
    Jiang, Hao
    Jorgensen, Karl Anker
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (25) : 6890 - 6899
  • [6] Organocatalytic asymmetric conjugate additions
    Almasi, Diana
    Alonso, Diego A.
    Najera, Carmen
    [J]. TETRAHEDRON-ASYMMETRY, 2007, 18 (03) : 299 - 365
  • [7] 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
  • [8] Organocatalyzed Synthesis of Tertiary α-Hydroxyphosphonates by a Highly Regioselective Modified Pudovik Reaction
    Barros, Maria Teresa
    Phillips, Ana Maria Faisca
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (20-21) : 4028 - 4036
  • [9] Organocatalytic Asymmetric Hydrophosphonylation/Mannich Reactions Using Thiourea, Cinchona and Bronsted Acid Catalysts
    Bhadury, Pinaki S.
    Li, Hu
    [J]. SYNLETT, 2012, (08) : 1108 - 1131
  • [10] Synthesis of nonracemic dimethyl α-(hydroxyfarnesyl)phosphonates via oxidation of dimethyl farnesylphosphonate with (camphorsulfonyl)oxaziridines
    Cermak, DM
    Du, YM
    Wiemer, DF
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (02) : 388 - 393