Enantioselective Conjugate Addition of Nitroalkanes to Alkylidenemalonates Promoted by Thiourea-Based Bifunctional Organocatalysts

被引：24
|
作者：
Chiarucci, Michel [1 ]
Lombardo, Marco [1 ]
Trombini, Claudio [1 ]
Quintavalla, Arianna [1 ]
机构：
[1] Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2012年 / 354卷 / 2-3期
关键词：
alkylidenemalonates; asymmetric organocatalysis; bifunctional thioureas; Michael reaction; nitro compounds; ASYMMETRIC MICHAEL ADDITION; 1,3-DICARBONYL COMPOUNDS; ALPHA; BETA-UNSATURATED IMIDES; 1,4-ADDITION;
D O I：
10.1002/adsc.201100732
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
Cinchona alkaloids-derived bifunctional thioureas efficiently catalyse the enantioselective conjugate addition of nitroalkanes to alkylidenemalonates with syn-diastereopreference, opening a route to the synthesis of optically active ?-amino acid derivatives.
引用
收藏
页码：364 / 370
页数：7
相关论文
共 50 条
  • [21] The highly enantioselective bifunctional organocatalysts for the Michael addition of сyclohexanone to titroolefins
    M. Yang
    Y. C. Zhang
    J. Q. Zhao
    Q. S. Yang
    Y. Ma
    X. H. Cao
    Russian Journal of General Chemistry, 2016, 86 : 1381 - 1388
  • [22] Highly enantioselective conjugate addition of nitroalkanes to alkylidenemalonates using efficient phase-transfer catalysis of N-spiro chiral ammonium bromides
    1600, American Chemical Society, Columbus, United States (126):
  • [23] The highly enantioselective bifunctional organocatalysts for the Michael addition of Nyclohexanone to titroolefins
    Yang, M.
    Zhang, Y. C.
    Zhao, J. Q.
    Yang, Q. S.
    Ma, Y.
    Cao, X. H.
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2016, 86 (06) : 1381 - 1388
  • [24] Stereoselective nucleophilic addition to imines catalyzed by chiral bifunctional thiourea organocatalysts
    Puglisi, Alessandra
    Benaglia, Maurizio
    Annunziata, Rita
    Rossi, Davide
    TETRAHEDRON-ASYMMETRY, 2008, 19 (19) : 2258 - 2264
  • [25] Recent applications of thiourea-based organocatalysts in asymmetric multicomponent reactions (AMCRs)
    Parvin, Tasneem
    Yadav, Rahul
    Choudhury, Lokman H.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (29) : 5513 - 5532
  • [26] Organocatalytic enantioselective conjugate addition of nitroalkanes to trifluoromethylated 3-methyleneoxindoles
    Qin, Wen-Bing
    Lou, Qinxin
    Xiong, Wei
    Liu, Guo-Kai
    TETRAHEDRON LETTERS, 2020, 61 (43)
  • [27] Enantioselective Organocatalytic Conjugate Addition of Nitroalkanes to Electrophilic 2-Iminochromenes
    Li, Wenjun
    Liu, Hui
    Jiang, Xuefeng
    Wang, Jian
    ACS CATALYSIS, 2012, 2 (08): : 1535 - 1538
  • [28] Thiourea-based bifunctional organocatalysis: Supramolecular recognition for living polymerization
    Dove, AP
    Pratt, RC
    Lohmeijer, BGG
    Waymouth, RM
    Hedrick, JL
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (40) : 13798 - 13799
  • [29] Thiourea-based bifunctional organocatalysis: Supramolecular recognition for living polymerization
    1600, American Chemical Society, Columbus, United States (127):
  • [30] Enantioselective Michael Addition of Nitroalkanes to Nitroalkenes Catalyzed by Chiral Bifunctional Quinine-Based Squaramides
    Kanberoglu, Esra
    Tanyeli, Cihangir
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 5 (01) : 114 - 119
12345