An asymmetric domino three-component synthesis of β-lactams

被引：0
|
作者：
Palomo, C
Aizpurua, JM
Gracenea, JJ
Garcia-Granda, S
Pertierra, P
机构：
[1] Univ Basque Country, Fac Quim, Dept Quim Organ, E-20009 San Sebastian, Spain
[2] Univ Oviedo, Dept Quim Fis & Analit, E-33071 Oviedo, Spain
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 1998年 / 1998卷 / 10期
关键词：
antibiotics; asymmetric synthesis; beta-lactams; Michael additions; multicomponent reactions;
D O I：
10.1002/(SICI)1099-0690(199810)1998:10<2201::AID-EJOC2201>3.0.CO;2-R
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Lithium dialkylcuprates react either in a sequential one-pot or in a domino "three-component" fashion with chiral Michael accepters, Like Oppolzer's N-enoyl-2,10-camphorsultams 7 and 11 or Evans' N-enoyl-4-phenyl-1,3-oxazolidin-2-ones 8 and 13, and N-(methoxycarbonyl-methylidene)(4-methoxyphenyl)amine 9 to afford the corresponding cis-3-alkyl-4-methoxycarbonyl-1-(4-methoxyphenyl) azetidin-2-ones 10, 14-15 in overall yields of 40-67 % and enantiomeric excesses of 91-99 %.
引用
收藏
页码：2201 / 2207
页数：7
相关论文
共 50 条
  • [41] A three-component Fischer indole synthesis
    Christopher A Simoneau
    Bruce Ganem
    Nature Protocols, 2008, 3 : 1249 - 1252
  • [42] Regiodiverse Three-Component Synthesis of Arenes
    Danz, Michael
    Hilt, Gerhard
    ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (2-3) : 303 - 308
  • [43] A novel three-component tetrahydrobenzofuran synthesis
    Shaabani, A
    Teimouri, MB
    Bijanzadeh, HR
    MONATSHEFTE FUR CHEMIE, 2004, 135 (04): : 441 - 446
  • [44] A three-component Fischer indole synthesis
    Simoneau, Christopher A.
    Ganem, Bruce
    NATURE PROTOCOLS, 2008, 3 (08) : 1249 - 1252
  • [45] Three-component synthesis of homoallylic carbamates
    Kalita, HR
    Phukan, P
    SYNTHETIC COMMUNICATIONS, 2005, 35 (03) : 475 - 481
  • [46] A Novel Three-Component Tetrahydrobenzofuran Synthesis
    Ahmad Shaabani
    Mohammad B. Teimouri
    Hamid R. Bijanzadeh
    Monatshefte für Chemie / Chemical Monthly, 2004, 135 : 441 - 446
  • [47] Convergent Three-Component Tetrazole Synthesis
    Chandgude, Ajay L.
    Domling, Alexander
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (14) : 2383 - 2387
  • [48] Three-Component Fischer Indole Synthesis
    El Kaim, Laurent
    Grimaud, Laurence
    Ronsseray, Caroline
    SYNLETT, 2010, (15) : 2296 - 2298
  • [49] Three-Component Asymmetric Polymerization toward Chiral Polymer
    Li, Ming
    Duan, Xuelun
    Jiang, Yu
    Sun, Xinhao
    Xu, Xiang
    He, Junnan
    Zheng, Yubin
    Song, Wangze
    Zheng, Nan
    CCS CHEMISTRY, 2022, 4 (10): : 3402 - 3415
  • [50] Asymmetric, catalytic three-component assembly of allylic amines
    Patel, SJ
    Jamison, TF
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2004, 227 : U210 - U210
12345