New Prolinamides with Isosteviol Skeleton as Efficient Organocatalysts for the Direct Asymmetric Aldol Reaction

被引:3
|
作者
Liu, Yu-Xia [1 ]
Ma, Zhi-Wei [3 ]
Li, Yan-Xun [1 ]
Tao, Jing-Chao [2 ]
机构
[1] Henan Inst Engn, Dept Mat & Chem Engn, Zhengzhou 450007, Henan, Peoples R China
[2] Zhengzhou Univ, Dept Chem, New Drug Res & Dev Ctr, Zhengzhou 450052, Henan, Peoples R China
[3] Henan Univ Anim Husb & Econ, Dept Fundamental Courses, Zhengzhou 450044, Henan, Peoples R China
基金
中国国家自然科学基金;
关键词
Aldol reaction; asymmetric catalysis; isosteviol; organocatalyst; prolinamide; synthesis; 3-COMPONENT MANNICH REACTIONS; MICHAEL ADDITION; STEREOSELECTIVE-SYNTHESIS; AQUEOUS-MEDIUM; WATER; DERIVATIVES; CATALYSIS; ALDEHYDES; KETONES; ISOBUTYRALDEHYDE;
D O I
10.2174/1570178615666171226163338
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In this work, two new prolinamides with isosteviol skeleton were synthesized and used as chiral catalysts for the asymmetric aldol reaction. Solvent effects, catalyst loading, substrate scope and the influence of water on the reaction were investigated. With only 5 mol % loading, the synthesized catalysts showed excellent activity (up to 98% yield) and good stereoselectivity (up to 87:13 dr, 90% ee) for the direct aldol reaction of cyclohexanone and substituted benzaldehydes at room temperature.
引用
收藏
页码:307 / 313
页数:7
相关论文
共 50 条
  • [1] Prolinamides derived from aminophenols as organocatalysts for asymmetric direct aldol reactions
    Sathapornvajana, Sornpranart
    Vilaivan, Tirayut
    TETRAHEDRON, 2007, 63 (41) : 10253 - 10259
  • [2] Combining prolinamides with 2-pyrrolidinone: Novel organocatalysts for the asymmetric aldol reaction
    Vlasserou, Ismini
    Sfetsa, Maria
    Gerokonstantis, Dimitrios-Triantafyllos
    Kokotos, Christoforos G.
    Moutevelis-Minakakis, Panagiota
    TETRAHEDRON, 2018, 74 (19) : 2338 - 2349
  • [3] L-Prolinethioamides - Efficient organocatalysts for the direct asymmetric aldol reaction
    Gryko, D
    Lipinski, R
    ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (15) : 1948 - 1952
  • [4] Highly efficient organocatalysts for the asymmetric aldol reaction
    Jacoby, C. G.
    Vontobel, P. H. V.
    Bach, M. F.
    Schneider, P. H.
    NEW JOURNAL OF CHEMISTRY, 2018, 42 (09) : 7416 - 7421
  • [5] Highly efficient primary amine organocatalysts for the direct asymmetric aldol reaction in brine
    Ma, Xiao
    Da, Chao-Shan
    Yi, Lei
    Jia, Ya-Ning
    Guo, Qi-Peng
    Che, Li-Ping
    Wu, Feng-Chun
    Wang, Jun-Rui
    Li, Wei-Ping
    TETRAHEDRON-ASYMMETRY, 2009, 20 (12) : 1419 - 1424
  • [6] Highly efficient prollinamide-based organocatalysts for the direct asymmetric aldol reaction in brine
    Jia, Ya-Ning
    Wu, Feng-Chun
    Ma, Xiao
    Zhu, Gong-Jian
    Da, Chao-Shan
    TETRAHEDRON LETTERS, 2009, 50 (25) : 3059 - 3062
  • [7] The Ion Tag Strategy as a Route to Highly Efficient Organocatalysts for the Direct Asymmetric Aldol Reaction
    Lombardo, Marco
    Easwar, Srinivasan
    Pasi, Filippo
    Trombinia, Claudio
    ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (1-2) : 276 - 282
  • [8] Bisprolinediamides with the binaphthyl backbone as organocatalysts for the direct asymmetric Aldol reaction
    Gryko, Dorota
    Kowalczyk, Bartlomiej
    Zawadzki, Lukasz
    SYNLETT, 2006, (07) : 1059 - 1062
  • [9] Carbohydrate-based organocatalysts in direct asymmetric aqueous aldol reaction
    Mondal, Mohabul A.
    Mandal, Debashis
    JOURNAL OF CARBOHYDRATE CHEMISTRY, 2016, 35 (04) : 181 - 200
  • [10] New organocatalysts derived from tetrahydropapaverine for asymmetric aldol reaction
    Sedigheh Sadat Naeimi
    Peyman Salehi
    Morteza Bararjanian
    Journal of the Iranian Chemical Society, 2022, 19 : 3407 - 3416