N-Heterocyclic carbene-catalyzed (NHC) three-component domino reactions: highly stereoselective synthesis of functionalized acyclic ε-ketoesters

被引：18
|
作者：
Ma, Jianze
Huang, You [1 ]
Chen, Ruyu
机构：
[1] Nankai Univ, State Key Lab, Tianjin 300071, Peoples R China
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2011年 / 9卷 / 06期
基金：
中国国家自然科学基金;
关键词：
GAMMA-BUTYROLACTONES; ALPHA; BETA-UNSATURATED ALDEHYDES; ENANTIOSELECTIVE SYNTHESIS; THIOPHOSPHINYL IMINES; NUCLEOPHILIC CARBENES; 4+2 CYCLOADDITION; ENALS; HOMOENOLATE; CHEMISTRY; KETENES;
D O I：
10.1039/c0ob00725k
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel NHC-catalyzed three-component domino strategy to access high functionalized cis-epsilon-ketoesters with excellent yields (up to 98%) and high stereoselectivities (up to 20 : 1) is documented. The title domino reactions are atom economical and work on a broad range of substrates. The relative stereochemistry could be explained by a cascade crossed-benzoin/oxy-Cope rearrangement/esterification process. The thus-obtained products are of potential synthetic value in the drug research and combinatorial chemistry.
引用
收藏
页码：1791 / 1798
页数：8
相关论文
共 50 条
  • [1] N-Heterocyclic Carbene-Catalyzed Three-Component Domino Reaction of Alkynyl Aldehydes with Oxindoles
    Du, Ding
    Hu, Zhongyuan
    Jin, Jianlin
    Lu, Yingyan
    Tang, Weifang
    Wang, Bo
    Lu, Tao
    ORGANIC LETTERS, 2012, 14 (05) : 1274 - 1277
  • [2] N-Heterocyclic Carbene-Catalyzed Stereoselective Cascade Reaction: Synthesis of Functionalized Tetrahydroquinolines
    Zhang, Hai-Rui
    Dong, Zhen-Wen
    Yang, Yu-Jie
    Wang, Ping-Luan
    Hui, Xin-Ping
    ORGANIC LETTERS, 2013, 15 (18) : 4750 - 4753
  • [3] N-Heterocyclic Carbene-Catalyzed Redox Reactions of α-Functionalized Aldehydes
    Rong, Zi-Qiang
    Zhang, Wei
    Yang, Gui-Qiu
    You, Shu-Li
    CURRENT ORGANIC CHEMISTRY, 2011, 15 (17) : 3077 - 3090
  • [4] Stereoselective synthesis of spirocyclopentanones via N-heterocyclic carbene-catalyzed reactions of enals and dienones
    Nair, Vijay
    Babu, Beneesh Pattoorpadi
    Vellalath, Sreekumar
    Suresh, Eringathodi
    CHEMICAL COMMUNICATIONS, 2008, (06) : 747 - 749
  • [5] N-heterocyclic carbene-catalyzed radical reactions
    Kun-Quan Chen
    He Sheng
    Qiang Liu
    Pan-Lin Shao
    Xiang-Yu Chen
    Science China(Chemistry), 2021, 64 (01) : 7 - 16
  • [6] N-Heterocyclic Carbene Catalyzed Domino Reactions
    Grossmann, Andre
    Enders, Dieter
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (02) : 314 - 325
  • [7] N-heterocyclic carbene-catalyzed radical reactions
    Chen, Kun-Quan
    Sheng, He
    Liu, Qiang
    Shao, Pan-Lin
    Chen, Xiang-Yu
    SCIENCE CHINA-CHEMISTRY, 2021, 64 (01) : 7 - 16
  • [8] N-heterocyclic carbene-catalyzed radical reactions
    Kun-Quan Chen
    He Sheng
    Qiang Liu
    Pan-Lin Shao
    Xiang-Yu Chen
    Science China Chemistry, 2021, 64 : 7 - 16
  • [9] Ni/N-Heterocyclic Carbene-Catalyzed Enantioselective Three-Component Couplings of Aldehydes, Alkynes and Enones
    Zhou Zhijun
    Kong Wangqing
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2022, 42 (03) : 913 - 914
  • [10] Organocatalytic Three-Component Acyldifluoromethylation of Vinylarenes via N-Heterocyclic Carbene-Catalyzed Radical Relay
    She, Kun
    Liang, Feng
    Tian, Shichao
    Wang, Hengshan
    Tsui, Gavin Chit
    Wang, Quande
    ORGANIC LETTERS, 2022, : 4840 - 4844
12345