Organocatalytic one-pot asymmetric synthesis of 2-aryl-2,3-dihydro-4-quinolones

被引:16
|
作者
Pan, Gao-Fei [1 ]
Su, Li [1 ]
Zhang, Yan-Lei [1 ]
Guo, Shi-Huan [1 ]
Wang, Yong-Qiang [1 ]
机构
[1] Northwest Univ, Dept Chem & Mat Sci, Minist Educ, Key Lab Synthet & Nat Funct Mol Chem, Xian 710069, Peoples R China
来源
RSC ADVANCES | 2016年 / 6卷 / 30期
基金
中国国家自然科学基金;
关键词
AZA-MICHAEL ADDITION; ENANTIOSELECTIVE SYNTHESIS; ANTITUMOR AGENTS; 2-SUBSTITUTED 2,3-DIHYDRO-4-QUINOLONES; QUINOLIZIDINE ALKALOIDS; DERIVATIVES; INDOLIZIDINE; CYCLIZATION; FLAVANONES; CATALYSIS;
D O I
10.1039/c6ra01247g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A highly efficient organocatalytic one-pot enantioselective synthesis of (R)-2-aryl-2,3-dihydro-4-quinolones from o-aminoacetophenones and aryl aldehydes has been developed. The approach is characterized by beingmetal free, solvent free and protecting group free. A variety of 2-aryl-2,3-dihydro-4-quinolones could be obtained in good yields up to 99% ee.
引用
收藏
页码:25375 / 25378
页数:4
相关论文
共 50 条
  • [21] One-pot organocatalytic direct asymmetric synthesis of γ-AminoAlcohol derivatives
    Cordova, Armando
    SYNLETT, 2007, (13) : 2146 - 2146
  • [22] Cyclization vs. Elimination Reactions of 5-Aryl-5-hydroxy 1,3-Diones: One-Pot Synthesis of 2-Aryl-2,3-dihydro-4H-pyran-4-ones
    Khera, Rasheed Ahmad
    Ahmad, Rasheed
    Ullah, Ihsan
    Abid, Obaid-Ur-Rahman
    Fatunsin, Olumide
    Sher, Muhammad
    Villinger, Alexander
    Langer, Peter
    HELVETICA CHIMICA ACTA, 2010, 93 (09) : 1705 - 1715
  • [23] Organocatalytic One-Pot Asymmetric Synthesis of 4H,5H-Pyrano[2,3-c]pyrazoles
    Enders, Dieter
    Grossmann, Andre
    Gieraths, Bianca
    Duezdemir, Muharrem
    Merkens, Carina
    ORGANIC LETTERS, 2012, 14 (16) : 4254 - 4257
  • [24] Chiral Phosphoric Acid Catalyzed Asymmetric Synthesis of 2-Substituted 2,3-Dihydro-4-quinolones by a Protecting-Group-Free Approach
    Saito, Kodai
    Moriya, Yuka
    Akiyama, Takahiko
    ORGANIC LETTERS, 2015, 17 (13) : 3202 - 3205
  • [25] One-pot synthesis of 2,3-Dihydro-1H-benzimidazoles
    Ryabukhin, Sergey V.
    Plaskon, Andrey S.
    Volochnyuk, Dmitry M.
    Shivanyuk, Alexander N.
    Tolmachev, Andrey A.
    JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (19): : 7417 - 7419
  • [26] A one-pot organocatalytic asymmetric entry to tetrahydrothioxanthenones
    Rios, Ramon
    Sunden, Henrik
    Ibrahem, Ismail
    Zhao, Gui-Ling
    Cordova, Armando
    TETRAHEDRON LETTERS, 2006, 47 (49) : 8679 - 8682
  • [27] An Asymmetric Organocatalytic One-Pot Strategy to Octahydroacridines
    Dickmeiss, Gustav
    Jensen, Kim L.
    Worgull, Dennis
    Franke, Patrick T.
    Jorgensen, Karl Anker
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (07) : CP1 - CP4
  • [28] Asymmetric Alkaloid Synthesis: A One-Pot Organocatalytic Reaction to Quinolizidine Derivatives
    Franzen, Johan
    Fisher, Andreas
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (04) : 787 - 791
  • [29] One-pot organocatalytic direct asymmetric synthesis of γ-amino alcohol derivatives
    Córdova, A
    SYNLETT, 2003, (11) : 1651 - 1654
  • [30] A one-pot asymmetric organocatalytic tandem reaction for the synthesis of oxazine derivatives
    Jin, Zhichao
    Yu, Feng
    Wang, Xiao
    Huang, Huicai
    Luo, Xiaoyan
    Liang, Xinmiao
    Ye, Jinxing
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (06) : 1809 - 1816