Asymmetric Stepwise Reductive Amination of Aryl N-Heteroaryl Ketones with Benzyl Amines via Iridium Catalysis

被引：8
|
作者：
Yang, Bing [1 ]
Fu, Hao [1 ]
Yuan, Jing [2 ]
Wen, Simiaomiao [1 ]
Wang, Chunqin [2 ]
Liu, Qixing [1 ]
Zhou, Haifeng [1 ]
机构：
[1] China Three Gorges Univ, Coll Biol & Pharmaceut Sci, Hubei Key Lab Nat Prod Res & Dev, Res Ctr Green Pharmaceut Technol & Proc, Yichang 443002, Peoples R China
[2] Yichang Humanwell Pharmaceut Co Ltd, Yichang 443005, Peoples R China
来源：
ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 10卷 / 11期
关键词：
Asymmetric reductive amination; Aryl N-heteroaryl methylamines; Iridium; Enantioselectivity; ONE-POT SYNTHESIS; TRANSFER HYDROGENATION; ALLYLIC ALCOHOLS; CHIRAL ALCOHOLS; OLEFIN LIGANDS; ALKYNES; ACID;
D O I：
10.1002/ajoc.202100472
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An asymmetric reductive amination of aryl N-heteroaryl ketones with Benzyl Amines has been realized via one-pot two-step process, using p-toluenesulfonic acid and chiral iridium complexes as catalysts, a mixture of formic acid/triethylamine as a reductant. Twenty-three examples of chiral aryl N-heteroaryl methylamines were obtained with good yields and up to 99% ee.
引用
收藏
页码：2950 / 2953
页数：4
相关论文
共 50 条
  • [41] Practical N-alkylation via homogeneous iridium-catalyzed direct reductive amination
    Jing Wang
    Wenji Wang
    Xiongyu Yang
    Jingwen Liu
    Haizhou Huang
    Mingxin Chang
    Science China(Chemistry), 2023, (02) : 518 - 525
  • [42] Practical N-alkylation via homogeneous iridium-catalyzed direct reductive amination
    Jing Wang
    Wenji Wang
    Xiongyu Yang
    Jingwen Liu
    Haizhou Huang
    Mingxin Chang
    Science China Chemistry, 2023, 66 : 518 - 525
  • [43] Catalytic Asymmetric Reductive Amination for Axially Chiral Aryl Aldehydes via Desymmetrization/Kinetic Resolution Cascade
    Wang, Yi
    Song, Rui-Ping
    Li, Xin-Yue
    Chen, Wen-Li
    Tian, Yu
    Zhang, Shu-Hui
    Shao, You-Dong
    Cheng, Dao-Juan
    ORGANIC LETTERS, 2024, 26 (34) : 7161 - 7165
  • [44] A Simple and Efficient Ligand-Free Copper-Catalyzed C-N Bond Formation of Aryl (Hetero) Halides and N-Heteroaryl Amines
    Kommuri, Venkata Chandrasekhar
    Tadiparthi, Krishnaji
    Pawar, Lokesh
    Arunachalampillai, Athimoolam
    POLYCYCLIC AROMATIC COMPOUNDS, 2023, 43 (01) : 665 - 673
  • [45] Synthesis of ring-substituted N-benzyl γ-phenyl GABA derivatives via reductive amination
    Ramachandran, P. Veeraraghavan
    Sakavuyi, Kaumba
    Mistry, Hitesh
    FUTURE MEDICINAL CHEMISTRY, 2011, 3 (02) : 155 - 162
  • [46] Asymmetric reductive amination:: Convenient access to enantioenriched alkyl-alkyl or aryl-alkyl substituted α-chiral primary amines
    Nugent, Thomas C.
    Ghosh, Abhijit K.
    Wakchaure, Vijay N.
    Mohanty, Rashmi R.
    ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (10-11) : 1289 - 1299
  • [47] Cycloruthenation of aryl imines and N-heteroaryl benzenes via C-H bond activation with Ru(II) and acetate partners
    Li, Bin
    Darcel, Christophe
    Roisnel, Thierry
    Dixneuf, Pierre H.
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2015, 793 : 200 - 209
  • [48] Modular synthesis of α-aryl β-perfluoroalkyl ketones via N-heterocyclic carbene catalysis
    Yang, Hai-Bin
    Wang, Zhi-Hou
    Li, Jin-Mei
    Wu, Chuande
    CHEMICAL COMMUNICATIONS, 2020, 56 (26) : 3801 - 3804
  • [49] Construction of N-Aryl-Substituted Pyrrolidines by Successive Reductive Amination of Diketones via Transfer Hydrogenation
    Liao, Jianhua
    Tong, Jinghui
    Liu, Liang
    Ouyang, Lu
    Luo, Renshi
    MOLECULES, 2024, 29 (11):
  • [50] Copper-catalyzed asymmetric allylic amination: A novel method for chiral N-aryl allyl amines
    Murru, Siva
    Srivastava, Radhey S.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 244
12345