N-Heterocyclic Carbene Catalyzed Domino Reactions

被引:877
|
作者
Grossmann, Andre [1 ]
Enders, Dieter [1 ]
机构
[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
关键词
asymmetric catalysis; carbenes; domino reactions; organocatalysis; umpolung; STETTER-ALDOL-MICHAEL; ALPHA; BETA-UNSATURATED ALDEHYDES; FORMYLCYCLOPROPANE 1,1-DIESTERS; STEREOSELECTIVE-SYNTHESIS; ORGANOCATALYTIC SYNTHESIS; OXIDATIVE ESTERIFICATION; NUCLEOPHILIC CARBENES; ASYMMETRIC-SYNTHESIS; CONJUGATE ADDITIONS; RING EXPANSION;
D O I
10.1002/anie.201105415
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
While organocatalyzed domino reactions or organocascade catalysis developed into an important tool in synthetic chemistry during the past decade, the utility of N-heterocyclic carbenes (NHCs) as catalysts in domino reactions has only received growing attention in the past three years. Taking into account the unique activation modes of the substrates by NHC catalysts, it is often difficult to distinguish between a single chemical transformation and a sequential one-pot transformation. Therefore, herein we present a critical consideration of domino, cascade, and tandem catalysis in the case of NHC catalysts and highlight recent publications in this area.
引用
收藏
页码:314 / 325
页数:12
相关论文
共 50 条
  • [1] N-Heterocyclic Carbene Catalyzed Activation of Esters: A New Option for Asymmetric Domino Reactions
    Chauhan, Pankaj
    Enders, Dieter
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (06) : 1485 - 1487
  • [2] N-Heterocyclic Carbene Catalyzed Quadruple Domino Reactions: Asymmetric Synthesis of Cyclopenta[c]chromenones
    Liu, Qiang
    Chen, Xiang-Yu
    Puttreddy, Rakesh
    Rissanen, Kari
    Enders, Dieter
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (52) : 17100 - 17103
  • [3] N-heterocyclic carbene-catalyzed radical reactions
    Kun-Quan Chen
    He Sheng
    Qiang Liu
    Pan-Lin Shao
    Xiang-Yu Chen
    [J]. Science China Chemistry, 2021, 64 (01) : 7 - 16
  • [4] N-heterocyclic carbene-catalyzed radical reactions
    Chen, Kun-Quan
    Sheng, He
    Liu, Qiang
    Shao, Pan-Lin
    Chen, Xiang-Yu
    [J]. SCIENCE CHINA-CHEMISTRY, 2021, 64 (01) : 7 - 16
  • [5] N-heterocyclic carbene-catalyzed radical reactions
    Kun-Quan Chen
    He Sheng
    Qiang Liu
    Pan-Lin Shao
    Xiang-Yu Chen
    [J]. Science China Chemistry, 2021, 64 : 7 - 16
  • [6] N-Heterocyclic carbene-catalyzed domino hydroacylation/Stetter reactions of salicyl alkynylphosphonates and aromatic aldehydes
    Wang, Zhen-Qiang
    Wang, Ying
    Shi, De-Qing
    [J]. ARKIVOC, 2013, : 88 - 97
  • [7] Asymmetric Synthesis of Cyclopentene-Fused Tetrahydroquinolines via N-Heterocyclic Carbene Catalyzed Domino Reactions
    Zhao, Long
    Li, Sun
    Wang, Lei
    Yu, Shun
    Raabe, Gerhard
    Enders, Dieter
    [J]. SYNTHESIS-STUTTGART, 2018, 50 (13): : 2523 - 2532
  • [8] N-Heterocyclic Carbene Catalyzed Domino Cyclization of Propargylic Alcohols and Benzoyl Isocyanates
    Jo, Kyoung A.
    Maheswara, Muchchintala
    Yoon, Eunyoung
    Lee, Yun Yeong
    Yun, Hoseop
    Kang, Eun Joo
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (06): : 2924 - 2928
  • [9] N-heterocyclic carbene-catalyzed arene formation reactions
    Tingting Li
    Zhichao Jin
    Yonggui Robin Chi
    [J]. Science China Chemistry, 2022, 65 (02) : 210 - 223
  • [10] N-heterocyclic carbene-catalyzed arene formation reactions
    Tingting Li
    Zhichao Jin
    Yonggui Robin Chi
    [J]. Science China Chemistry, 2022, 65 : 210 - 223