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
  • [21] Highly enantioselective desymmetrization of meso- and prochiral cyclic ketones via organocatalytic Michael reaction
    Chen, Jia-Rong
    Lai, Yuan-Yuan
    Lu, Hai-Hua
    Wang, Xu-Fan
    Xiao, Wen-Jing
    TETRAHEDRON, 2009, 65 (45) : 9238 - 9243
  • [22] Highly Enantioselective Organocatalytic α-Sulfenylation of Azlactones
    Qiao, Baokun
    Liu, Xinfei
    Duan, Shaobo
    Yan, Lin
    Jiang, Zhiyong
    ORGANIC LETTERS, 2014, 16 (03) : 672 - 675
  • [23] Direct organocatalytic α-fluorination of aldehydes and ketones
    Enders, D
    Hüttl, MRM
    SYNLETT, 2005, (06) : 991 - 993
  • [24] Direct, organocatalytic α-sulfenylation of aldehydes and ketones
    Wang, W
    Li, H
    Wang, H
    Liao, LX
    TETRAHEDRON LETTERS, 2004, 45 (44) : 8229 - 8231
  • [25] Direct organocatalytic hydroalkoxylation of α,β-unsaturated ketones
    Ramachary, Dhevalapally B.
    Mondal, Rumpa
    TETRAHEDRON LETTERS, 2006, 47 (44) : 7689 - 7693
  • [26] The direct and enantioselective organocatalytic α-oxidation of aldehydes
    1600, American Chemical Society (125):
  • [27] Enantioselective Organocatalytic Michael Addition of Ketones to Alkylidene Malonates
    Syu, Siang-En
    Huang, Chan-Hui
    Chen, Ko-Wei
    Lee, Chia-Jui
    Das, Utpal
    Jang, Yeong-Jiunn
    Lin, Wenwei
    CHIRALITY, 2012, 24 (08) : 600 - 605
  • [28] ENANTIOSELECTIVE ORGANOCATALYTIC MICHAEL ADDITION OF ALIPHATIC KETONES TO NITRODIENES
    He, Tianxiong
    Wu, Xin-Yan
    SYNTHETIC COMMUNICATIONS, 2012, 42 (05) : 667 - 677
  • [29] Enantioselective Organocatalytic Conjugate Addition of Aromatic Ketones to Nitrodienes
    He, Tianxiong
    Qian, Jing-Ying
    Song, Hong-Liang
    Wu, Xin-Yan
    SYNLETT, 2009, (19) : 3195 - 3197
  • [30] The direct and enantioselective organocatalytic α-oxidation of aldehydes
    Brown, SP
    Brochu, MP
    Sinz, CJ
    MacMillan, DWC
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (36) : 10808 - 10809
12345