Direct catalytic asymmetric aldol reactions on chiral catalysts assembled in the interface of emulsion droplets

被引:72
|
作者
Zhong, Lin
Gao, Qiang
Gao, Jinbo
Xiao, Jianliang
Li, Can [1 ]
机构
[1] Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Catalysis, Dalian 116023, Peoples R China
[2] Univ Liverpool, Dept Chem, Liverpool L69 7ZD, Merseyside, England
基金
中国国家自然科学基金;
关键词
aldol reaction; asymmetric synthesis; emulsion catalysis; interface;
D O I
10.1016/j.jcat.2007.06.017
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
An amphiphilic proline-based organocatalyst was assembled on the interface of water and oil, resulting in a W/O emulsion. The chiral catalyst in emulsion significantly enhances the reactivity and stereoselectivity of the direct asymmetric aldol reactions, which can be attributed mainly to the larger interfacial surface area and uniformly distributed catalyst molecules in the interface of the emulsion droplets. (c) 2007 Elsevier Inc. All rights reserved.
引用
收藏
页码:360 / 364
页数:5
相关论文
共 50 条
  • [41] The 4,5-methano-L-proline as a chiral organocatalysts in direct asymmetric aldol reactions
    Yu, Na
    Han, Sheng
    Yu, Han
    TETRAHEDRON, 2015, 71 (28) : 4665 - 4669
  • [42] The Synthesis of Chiral Isotetronic Acids with Amphiphilic Imidazole/Pyrrolidine Catalysts Assembled in Oil-in-Water Emulsion Droplets
    Zhang, Boyu
    Jiang, Zongxuan
    Zhou, Xin
    Lu, Shengmei
    Li, Jun
    Liu, Yan
    Li, Can
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (52) : 13159 - 13162
  • [43] Catalytic asymmetric Mukaiyama aldol reactions in aqueous media
    Kobayashi, S
    Nagayama, S
    Busujima, T
    TETRAHEDRON, 1999, 55 (29) : 8739 - 8746
  • [44] Direct Catalytic Asymmetric Aldol Reaction of α-Vinyl Acetamide
    Takeuchi, Toshifumi
    Kumagai, Naoya
    Shibasaki, Masakatsu
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (10): : 5851 - 5858
  • [45] Direct Catalytic Asymmetric Aldol Reaction of an -Azido Amide
    Weidner, Karin
    Sun, Zhongdong
    Kumagai, Naoya
    Shibasaki, Masakatsu
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (21) : 6236 - 6240
  • [46] Asymmetric catalysis in aqueous media: Use of metal-chiral crown ethers as efficient chiral Lewis acid catalysts in asymmetric aldol reactions
    Kobayashi, S
    Hamada, T
    Nagayama, S
    Manabe, K
    JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2001, 12 (05) : 627 - 633
  • [47] Asymmetric, Regioselective Direct Aldol Coupling of Enones and Aldehydes with Chiral Rhodium(bis-oxazolinylphenyl) Catalysts
    Mizuno, Masato
    Inoue, Hiroko
    Naito, Tatsuo
    Zhou, Li
    Nishiyama, Hisao
    CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (36) : 8985 - 8988
  • [48] Direct Catalytic Asymmetric Synthesis of Oxindole-Derived δ-Hydroxy-β-ketoesters by Aldol Reactions
    Zhang, Dongxin
    Chen, Yan
    Cai, Hu
    Yin, Lei
    Zhong, Junchao
    Man, Jingjing
    Zhang, Qian-Feng
    Bethi, Venkati
    Tanaka, Fujie
    ORGANIC LETTERS, 2020, 22 (01) : 6 - 10
  • [49] CATALYTIC ASYMMETRIC ALDOL REACTIONS - USE OF A CHIRAL (ACYLOXY)BORANE COMPLEX AS A VERSATILE LEWIS ACID CATALYST
    FURUTA, K
    MARUYAMA, T
    YAMAMOTO, H
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (03) : 1041 - 1042
  • [50] Catalytic asymmetric aldol reactions in water using a chiral Lewis-acid-surfactant-combined catalyst
    Kobayashi, S
    Mori, Y
    Nagayama, S
    Manabe, K
    GREEN CHEMISTRY, 1999, 1 (04) : 175 - 177