Asymmetric intramolecular crossed-benzoin reactions by N-heterocyclic carbene catalysis

被引:248
|
作者
Enders, D [1 ]
Niemeier, O [1 ]
Balensiefer, T [1 ]
机构
[1] RWTH Aachen Univ, Inst Organ Chem, D-52074 Aachen, Germany
关键词
asymmetric synthesis; benzoin reaction; heterocycles; homogeneous catalysis; N-heterocyclic carbenes;
D O I
10.1002/anie.200503885
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Getting cross: Excellent asymmetric inductions and very good yields are achieved in the generation of a quaternary stereocenter in α-hydroxy-substituted tetralones by using chiral N-heterocyclic carbene catalysts in an enantioselective intramolecular crossed-benzoin reaction. The synthesis of the corresponding α-hydroxyindanones with good ee values is also possible by this route. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:1463 / 1467
页数:5
相关论文
共 50 条
  • [31] Smart N-Heterocyclic Carbene Ligands in Catalysis
    Peris, Eduardo
    CHEMICAL REVIEWS, 2018, 118 (19) : 9988 - 10031
  • [32] Designing successful monodentate N-heterocyclic carbene ligands for asymmetric metal catalysis
    Foster, Daven
    Borhanuddin, S. M.
    Dorta, Reto
    DALTON TRANSACTIONS, 2021, 50 (47) : 17467 - 17477
  • [33] Chiral N-heterocyclic carbene-transition metal complexes in asymmetric catalysis
    Perry, MC
    Burgess, K
    TETRAHEDRON-ASYMMETRY, 2003, 14 (08) : 951 - 961
  • [34] Aerobic oxidative N-heterocyclic carbene catalysis
    Stenkvist, Simon
    Bacaicoa, Sara
    Goossens, Ellymay
    Sunden, Henrik
    CHEMICAL RECORD, 2023, 23 (07):
  • [35] Dual Secondary Amine/N-Heterocyclic Carbene Catalysis in the Asymmetric Michael/Cross-Benzoin Cascade Reaction of β-Oxo Sulfones with Enals
    Enders, Dieter
    Grossmann, Andre
    Huang, He
    Raabe, Gerhard
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (23) : 4298 - 4301
  • [36] Theoretical investigation on the chemoselective N-heterocyclic carbene-catalyzed cross-benzoin reactions
    Liu, Tao
    Han, Shu-Min
    Han, Ling-Li
    Wang, Lu
    Cui, Xiang-Yang
    Du, Chong-Yang
    Bi, Siwei
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (12) : 3654 - 3661
  • [37] N-Heterocyclic Carbene Boryl Iodides Catalyze Insertion Reactions of N-Heterocyclic Carbene Boranes and Diazoesters
    Allen, Thomas H.
    Kawamoto, Takuji
    Gardner, Sean
    Geib, Steven J.
    Curran, Dennis P.
    ORGANIC LETTERS, 2017, 19 (13) : 3680 - 3683
  • [38] Synthesis of Homochiral N-Heterocyclic Carbene-Based Nanosheets for Enhanced Asymmetric Catalysis
    Wang, Xinchao
    Wang, Zhiwen
    Wang, Zhaoxing
    Liu, Tian-Fu
    Li, Shangda
    Wang, Fei
    Zhang, Jian
    ADVANCED SCIENCE, 2024,
  • [39] Chiral N-Heterocyclic Carbene Gold Complexes: Synthesis, Properties, and Application in Asymmetric Catalysis
    Banerjee, Dipshikha
    Buzas, Andrea K.
    Besnard, Celine
    Kuendig, E. Peter
    ORGANOMETALLICS, 2012, 31 (23) : 8348 - 8354
  • [40] Synthesis of Homochiral N-Heterocyclic Carbene-Based Nanosheets for Enhanced Asymmetric Catalysis
    Wang, Xinchao
    Wang, Zhiwen
    Wang, Zhaoxing
    Liu, Tian-Fu
    Li, Shangda
    Wang, Fei
    Zhang, Jian
    ADVANCED SCIENCE, 2025, 12 (02)