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
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2009年 / 48卷 / 48期
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
  • [1] Palladium-catalyzed enantioselective decarboxylative allylic alkylation of α-benzyl cyanoacetates: access to chiral acyclic quaternary carbon stereocenters
    Bao, Qing
    Sun, Ting-Jia
    Zhang, Yan-Ping
    Wang, Zhen-Hua
    You, Yong
    Ge, Zhen-Zhen
    Zhou, Ming-Qiang
    Zhao, Jian-Qiang
    Yuan, Wei-Cheng
    ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (23) : 5971 - 5977
  • [2] Palladium-Catalyzed Construction of Quaternary Stereocenters by Enantioselective Arylation of -Lactams with Aryl Chlorides and Bromides
    Jette, Carina I.
    Geibel, Irina
    Bachman, Shoshana
    Hayashi, Masaki
    Sakurai, Shunya
    Shimizu, Hideki
    Morgan, Jeremy B.
    Stoltz, Brian M.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (13) : 4297 - 4301
  • [3] Reactivity of bromoselenophenes in palladium-catalyzed direct arylations
    Skhiri, Aymen
    Ben Salem, Ridha
    Soule, Jean-Francois
    Doucet, Henri
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2017, 13 : 2862 - 2868
  • [4] Palladium-Catalyzed Direct Arylations of Heteroarenes with Tosylates and Mesylates
    Ackermann, Lutz
    Althammer, Andreas
    Fenner, Sabine
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (01) : 201 - 204
  • [5] Palladium-catalyzed enantioselective β-hydride elimination for the construction of remote stereocenters
    Sun, Shaozi
    Sun, Shengnan
    Zi, Weiwei
    NATURE COMMUNICATIONS, 2025, 16 (01)
  • [6] Palladium-Catalyzed Enantioselective Redox-Relay Heck Alkynylation of Alkenols To Access Propargylic Stereocenters
    Chen, Zhi-Min
    Nervig, Christine S.
    DeLuca, Ryan J.
    Sigman, Matthew S.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (23) : 6651 - 6654
  • [7] Enantioselective, Palladium-Catalyzed Conjugate Additions of Arylboronic Acids to Form Bis-benzylic Quaternary Stereocenters
    Kadam, Abhishek A.
    Ellern, Arkady
    Stanley, Levi M.
    ORGANIC LETTERS, 2017, 19 (15) : 4062 - 4065
  • [8] Fluorescent Diarylindoles by Palladium-Catalyzed Direct and Decarboxylative Arylations of Carboxyindoles
    Miyasaka, Mitsuru
    Fukushima, Azusa
    Satoh, Tetsuya
    Hirano, Koji
    Miura, Masahiro
    CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (15) : 3674 - 3677
  • [9] Palladium-catalyzed enantioselective carboannulation of 1,3-dienes with aryl iodides enables access to chiral indanes
    Wu, Xiang
    Chen, Shu-Sen
    Zhang, Ling
    Wang, Hai-Jun
    Gong, Liu-Zhu
    CHEMICAL COMMUNICATIONS, 2018, 54 (69) : 9595 - 9598
  • [10] Palladium-Catalyzed Transient Chirality Transfer and Atroposelective C-H Functionalization to Access Quaternary Stereocenters
    Han, Lu-Lu
    Cui, Yu-Ming
    Yang, Qin
    Fang, Li-Lei
    Xu, Li-Wen
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (46)
12345