Enantioselective Palladium-Catalyzed Direct Arylations at Ambient Temperature: Access to Indanes with Quaternary Stereocenters

被引:152
|
作者
Albicker, Martin R. [1 ]
Cramer, Nicolai [1 ]
机构
[1] ETH, Organ Chem Lab, CH-8093 Zurich, Switzerland
关键词
asymmetric catalysis; C-H activation; direct arylation; palladium; stereocenters; H BOND FUNCTIONALIZATION; PROTON-ABSTRACTION MECHANISM; C-H; ACTIVATION; ACID; EFFICIENT;
D O I
10.1002/anie.200905060
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Tadaa: The title reaction proceeds under essentially neutral reaction conditions at ambient temperature with a taddol-based phosphoramidite ligand L allowing the creation of indanes with quaternary stereogenic centers in high enantiomeric excess (see scheme; Tf=trifluoromethanesulfonyl, DMAc = dimethylacetamide). © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:9139 / 9142
页数:4
相关论文
共 50 条
  • [21] Influence of 1,3-Difluorobenzene Substituents for Palladium-Catalyzed Direct Arylations
    Yan, Tao
    Bheeter, Charles Beromeo
    Doucet, Henri
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (31) : 7152 - 7163
  • [22] Reactivity of Para-Substituted Fluorobenzenes in Palladium-catalyzed Intermolecular Direct Arylations
    He, Mian
    Soule, Jean-Francois
    Doucet, Henri
    CHEMCATCHEM, 2015, 7 (14) : 2130 - 2140
  • [23] Enantioselective Access to γ-All-Carbon Quaternary Center-Containing Cyclohexanones by Palladium-Catalyzed Desymmetrization
    Wei, Qiang
    Cai, Jinhui
    Hu, Xu-Dong
    Zhao, Jing
    Cong, Hengjiang
    Zheng, Chao
    Liu, Wen-Bo
    ACS CATALYSIS, 2020, 10 (01): : 216 - 224
  • [24] Palladium-Catalyzed Asymmetric Decarboxylative Cycloaddition of Vinylethylene Carbonates with Electrophiles: Construction of Quaternary Stereocenters
    Khan, Ajmal
    Zhang, Yong Jian
    SYNLETT, 2015, 26 (07) : 853 - 860
  • [25] Palladium-Catalyzed Asymmetric Desymmetrization for the Simultaneous Construction of Chiral Phosphorus and Quaternary Carbon Stereocenters
    Zhou, Hengrui
    Xue, Yiji
    Zhou, Xiang
    Yao, Hequan
    Lin, Aijun
    ORGANIC LETTERS, 2024, 26 (28) : 5934 - 5939
  • [26] Access to β-keto esters and 1,3-diketones by palladium-catalyzed carbonylative α-arylations
    Korsager, Signe
    Nielsen, Dennis U.
    Skrydstrup, Troels
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
  • [27] Pd-catalyzed enantioselective access to hydrocarbazolones containing contiguous quaternary and tertiary stereocenters
    Sun, Hao
    Yu, Cheng-Long
    Zheng, Yu-Qing
    Shu, Peng-Fei
    Dong, Zhan
    Xia, Yu-Chen
    Liu, Wen-Bo
    CHEMICAL SCIENCE, 2025, 16 (15) : 6425 - 6433
  • [28] Enantioselective palladium-catalyzed transformations
    Tietze, LF
    Ila, H
    Bell, HP
    CHEMICAL REVIEWS, 2004, 104 (07) : 3453 - 3516
  • [29] Direct Access to Furoindolines by Palladium-Catalyzed Intermolecular Carboamination
    Bizet, Vincent
    Borrajo-Calleja, Gustavo M.
    Besnard, Celine
    Mazet, Clement
    ACS CATALYSIS, 2016, 6 (10): : 7183 - 7187
  • [30] Recent Advances in the Construction of Quaternary Stereocenters via Palladium-Catalyzed Decarboxylative Asymmetric Allylic Alkylation
    Yu, Xinhui
    Zhang, Ting
    Liu, Jitian
    Li, Xiaoxun
    SYNTHESIS-STUTTGART, 2021, 53 (23): : 4341 - 4352