Efficient diastereoselective intermolecular rhodium-catalyzed C-H amination

被引:218
|
作者
Liang, Chungen
Robert-Pedlard, Fabien
Fruit, Corinne
Mueller, Paul
Dodd, Robert H.
Dauban, Philippe
机构
[1] Univ Geneva, Dept Organ Chem, CH-1211 Geneva 4, Switzerland
[2] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France
关键词
amination; C-H insertion; hypervalent iodine; nitrenes; rhodium;
D O I
10.1002/anie.200601248
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Successful matchmaking: The combination of a chiral nitrene precursor with a chiral rhodium(II) catalyst is the key factor that allows efficient intermolecular regioselective C-H amination. Good-to-excellent yields and excellent diastereoselectivities can be obtained with a stoichiometric amount of the C-H bond containing substrate. nttl = N-1,8-naphthoyl-tert-leucine. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:4641 / 4644
页数:4
相关论文
共 50 条
  • [41] Mechanism of the rhodium-catalyzed silylation of arene C-H bonds
    Hartwig, John F., 1600, American Chemical Society (136):
  • [42] Rhodium-Catalyzed Directed Sulfenylation of Arene C-H Bonds
    Yang, Yaxi
    Hou, Wei
    Qin, Lihuai
    Du, Juanjuan
    Feng, Huijin
    Zhou, Bing
    Li, Yuanchao
    CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (02) : 416 - 420
  • [43] Rhodium-Catalyzed C-H Alkynylation of Arenes at Room Temperature
    Feng, Chao
    Loh, Teck-Peng
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (10) : 2722 - 2726
  • [44] Rhodium-Catalyzed C-H Activation Enabled by an Indium Metalloligand
    Yamada, Ryosuke
    Iwasawa, Nobuharu
    Takaya, Jun
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (48) : 17251 - 17254
  • [45] Mechanistic insights into the rhodium-catalyzed aryl C-H carboxylation
    Liu, DeGuang
    Xu, ZheYuan
    Liu, MingQiang
    Fu, Yao
    ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (02) : 370 - 379
  • [46] Rhodium-Catalyzed Selective C-H Bond Functionalization of Quinolines
    Dhiman, Ankit K.
    Thakur, Ankita
    Kumar, Rakesh
    Sharma, Upendra
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 9 (10) : 1502 - 1518
  • [47] Mechanism of the Rhodium-Catalyzed Silylation of Arene C-H Bonds
    Cheng, Chen
    Hartwig, John F.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (34) : 12064 - 12072
  • [48] Electrochemical Rhodium-Catalyzed Enantioselective C-H Annulation with Alkynes
    Huang, Yuan-Qiong
    Wu, Zhi-Jie
    Zhu, Li
    Gu, Qing
    Lu, Xiaojie
    You, Shu-Li
    Mei, Tian-Sheng
    CCS CHEMISTRY, 2022, 4 (09): : 3181 - 3189
  • [49] Rhodium-catalyzed direct C-H amination of 2-arylindoles and 7-arylindoles with free amines
    Qin, Yao
    Zhuang, Weihui
    Guo, Xiemin
    Zhang, Xiaofeng
    Huang, Qiufeng
    TETRAHEDRON LETTERS, 2021, 62
  • [50] Diastereoselective Carbocyclization of 1,6-Heptadienes Triggered by Rhodium-Catalyzed Activation of an Olefinic C-H Bond
    Aissa, Christophe
    Ho, Kelvin Y. T.
    Tetlow, Daniel J.
    Pin-No, Maria
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (16) : 4209 - 4212