Highly enantioselective direct organocatalytic α-chlorination of ketones

被引：111
|
作者：
Marigo, M [1 ]
Bachmann, S [1 ]
Halland, N [1 ]
Braunton, A [1 ]
Jorgensen, KA [1 ]
机构：
[1] Aarhus Univ, Dept Chem, Ctr Catalysis, Danish Natl Res Fdn, DK-8000 Aarhus C, Denmark
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2004年 / 43卷 / 41期
关键词：
asymmetric catalysis; halogenation; homogeneous catalysis; ketones;
D O I：
10.1002/anie.200460462
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A C2-symmetric diamine serves as the organocatalyst in an asymmetric α-chlorination reaction of simple ketones (e.g., cyclohexanone, diethyl ketone). Optically active α-chloroketones are formed with excellent enantioselectivities using N-chlorosuccinimide (NCS) as the chlorine source (see scheme). These products have broad synthetic utility, in particular for pharmaceutical applications.
引用
收藏
页码：5507 / 5510
页数：4
相关论文
共 50 条
  • [41] Enantioselective desymmetrization of prochiral ketones via an organocatalytic deprotonation process
    Claraz, Aurelie
    Oudeyer, Sylvain
    Levacher, Vincent
    TETRAHEDRON-ASYMMETRY, 2013, 24 (12) : 764 - 768
  • [42] Organocatalytic enantioselective decarboxylative Michael addition of β-ketoacids to α,β-unsaturated ketones
    Kang, Young Ku
    Lee, Hyun Joo
    Moon, Hyoung Wook
    Kim, Dae Young
    RSC ADVANCES, 2013, 3 (05) : 1332 - 1335
  • [43] Direct Organocatalytic Enantioselective Functionalization of SiOx Surfaces
    Parkin, John D.
    Chisholm, Ross
    Frost, Aileen B.
    Bailey, Richard G.
    Smith, Andrew D.
    Haehner, Georg
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (30) : 9377 - 9381
  • [44] Organocatalytic Enantioselective Vinylogous Aldol Reaction of Allyl Aryl Ketones to Activated Acyclic Ketones
    Jing, Zhenzhong
    Bai, Xiangbin
    Chen, Wenchao
    Zhang, Gao
    Zhu, Bo
    Jiang, Zhiyong
    ORGANIC LETTERS, 2016, 18 (02) : 260 - 263
  • [45] Highly Enantioselective Construction of Fluoroalkylated Quaternary Stereocenters via Organocatalytic Dehydrated Mannich Reaction of Unprotected Hemiaminals with Ketones
    Zhang, Sheng
    Li, Lijun
    Hu, Yanbin
    Li, Yanan
    Yang, Yu
    Zha, Zhenggen
    Wang, Zhiyong
    ORGANIC LETTERS, 2015, 17 (20) : 5036 - 5039
  • [46] Highly enantioselective catalytic reduction of ketones
    Adolfsson, H
    Bogevig, A
    Västilä, P
    Pastor, IM
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2004, 227 : U204 - U204
  • [47] Direct catalytic enantioselective α-aminomethylation of ketones
    Ibrahem, I
    Casas, J
    Córdova, A
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (47) : 6528 - 6531
  • [48] Highly Enantioselective and Organocatalytic α-Amination of 2-Oxindoles
    Cheng, Liang
    Liu, Li
    Wang, Dong
    Chen, Yong-Jun
    ORGANIC LETTERS, 2009, 11 (17) : 3874 - 3877
  • [49] Organocatalytic highly enantioselective nitroaldol reaction of α-ketophosphonates and nitromethane
    Mandal, Tanmay
    Samanta, Sampak
    Zhao, Cong-Gui
    ORGANIC LETTERS, 2007, 9 (05) : 943 - 945
  • [50] Enantioselective organocatalytic reductive amination of aliphatic ketones by benzothiazoline as hydrogen donor
    Saito, Kodai
    Akiyama, Takahiko
    CHEMICAL COMMUNICATIONS, 2012, 48 (38) : 4573 - 4575
12345