Catalytic asymmetric Horner-Wadsworth-Emmons reaction under phase-transfer-catalyzed conditions

被引：80
|
作者：
Arai, S [1 ]
Hamaguchi, S [1 ]
Shioiri, T [1 ]
机构：
[1] Nagoya City Univ, Fac Pharmaceut Sci, Mizuho Ku, Nagoya, Aichi 4678603, Japan
来源：
TETRAHEDRON LETTERS | 1998年 / 39卷 / 19期
关键词：
asymmetric reactions; catalysts; olefination; phase transfer;
D O I：
10.1016/S0040-4039(98)00442-0
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The catalytic asymmetric Homer-Wadsworth-Emmons reaction promoted by quaternary ammonium salts derived from cinchonine as a phase-transfer catalyst is described. Treatment of the prochiral ketone 1 with phosphonates under mild reaction conditions afforded the corresponding desired products in moderate enantiomeric excess. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：2997 / 3000
页数：4
相关论文
共 50 条
  • [1] Enantioselective preparation of allenecarboxylates by asymmetric Horner-Wadsworth-Emmons reaction
    Tetrahedron Lett, 21 (3735):
  • [2] Enantioselective preparation of allenecarboxylates by asymmetric Horner-Wadsworth-Emmons reaction
    Tanaka, K
    Otsubo, K
    Fuji, K
    TETRAHEDRON LETTERS, 1996, 37 (21) : 3735 - 3738
  • [3] The Asymmetric Horner-Wadsworth-Emmons Reaction Mediated by an External Chiral Ligand
    Grad. Sch. of Pharmaceutical Sci., Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-01, Japan
    Angew. Chem. Int. Ed., 4 (515-517):
  • [4] The asymmetric Horner-Wadsworth-Emmons reaction mediated by an external chiral ligand
    Mizuno, M
    Fujii, K
    Tomioka, K
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1998, 37 (04) : 515 - 517
  • [5] Recent Progress in the Horner-Wadsworth-Emmons Reaction
    Bisceglia, Juan A.
    Orelli, Liliana R.
    CURRENT ORGANIC CHEMISTRY, 2015, 19 (09) : 744 - 775
  • [6] Mechanism and kinetics of Horner-Wadsworth-Emmons reaction in liquid-liquid phase-transfer catalytic system
    Zhao, Qiangqiang
    Sun, Jie
    Li, Fuqiang
    He, Jinxin
    Liu, Baojiang
    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2015, 400 : 111 - 120
  • [7] ASYMMETRIC CARBOALKOXYALKYLIDENATION WITH A CHIRAL HORNER-WADSWORTH-EMMONS REAGENT
    DENMARK, SE
    RIVERA, I
    JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (23): : 6887 - 6889
  • [8] Regioselective catalytic asymmetric reaction of Horner-Wadsworth-Emmons reagents with enones: The odyssey of chiral aluminum catalysts
    Arai, T
    Sasai, H
    Yamaguchi, K
    Shibasaki, M
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (02) : 441 - 442
  • [9] A modified Horner-Wadsworth-Emmons reaction for the synthesis of nitroalkenes
    Franklin, AS
    SYNLETT, 2000, (08) : 1154 - 1156
  • [10] A quantum chemical exploration of the Horner-Wadsworth-Emmons reaction
    Brandt, P
    Norrby, PO
    Martin, I
    Rein, T
    JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (04): : 1280 - 1289
12345