Direct asymmetric aldol reaction catalyzed by simple prolinamide phenols

被引：94
|
作者：
Fu, Yu-Qin [1 ]
Li, Zai-Chun [1 ]
Ding, Ll-Na [1 ]
Tao, Jing-Chao [1 ]
Zhang, Sheng-Hong [1 ]
Tang, Ming-Sheng [1 ]
机构：
[1] Zhengzhou Univ, Dept Chem, New Drug Res & Dev Ctr, Zhengzhou 450052, Peoples R China
来源：
TETRAHEDRON-ASYMMETRY | 2006年 / 17卷 / 24期
基金：
中国国家自然科学基金;
关键词：
D O I：
10.1016/j.tetasy.2006.12.008
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Simple prolinamides 1a-f were synthesized, and their catalytic effects on the direct asymmetric aldol reactions in organic solvents and in water were evaluated. Prolinamide phenols 1a-d were found to be effective catalysts for the reaction of aromatic aldehydes with cyclohexanone in neat ketone and in water. The anti-aldol products were obtained with up to 98/2 anti/syn ratio and 96% ee in neat ketone, 98/2 anti/syn ratio and 99% ee in water, respectively. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3351 / 3357
页数：7
相关论文
共 50 条
  • [31] The direct catalytic asymmetric aldol reaction
    Alcaide, B
    Almendros, P
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2002, 2002 (10) : 1595 - 1601
  • [32] Recent progress in aldolase-mimic catalyzed direct asymmetric aldol reaction
    Zhang, J
    Li, LL
    Luo, MM
    Xie, RG
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2002, 22 (05) : 318 - 326
  • [33] Asymmetric direct aldol reaction of α-keto esters and acetone catalyzed by bifunctional organocatalysts
    Wang, Fei
    Xiong, Yan
    Liu, Xiaohua
    Feng, Xiaoming
    ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (17-18) : 2665 - 2668
  • [34] Asymmetric, Catalytic, and Direct Self-Aldol Reaction of Acetaldehyde Catalyzed by Diarylprolinol
    Hayashi, Yujiro
    Samanta, Sampak
    Itoh, Takahiko
    Ishikawa, Hayato
    ORGANIC LETTERS, 2008, 10 (24) : 5581 - 5583
  • [35] Preparation of Immobilized L-Prolinamide Via Enzymatic Polymerization of Phenolic L-Prolinamide and Evaluation of Its Catalytic Performance for Direct Asymmetric Aldol Reaction
    Qu, Chengke
    Zhao, Wenshan
    Zhang, Lei
    Cui, Yuanchen
    CHIRALITY, 2014, 26 (04) : 209 - 213
  • [36] Direct aldol reactions catalyzed by intramolecularly folded prolinamide dendrons: dendrimer effects on stereoselectivity
    Mitsui, Kazuhiko
    Hyatt, Sarah A.
    Turner, Daniel A.
    Hadad, Christopher M.
    Parquette, Jon R.
    CHEMICAL COMMUNICATIONS, 2009, (22) : 3261 - 3263
  • [37] Ion-Tagged Prolinamide Organocatalysts for the Direct Aldol Reaction On-Water
    Eyckens, Daniel J.
    Brozinski, Hannah L.
    Delaney, Joshua P.
    Servinis, Linden
    Naghashian, Sahar
    Henderson, Luke C.
    CATALYSIS LETTERS, 2016, 146 (01) : 212 - 219
  • [38] Ion-Tagged Prolinamide Organocatalysts for the Direct Aldol Reaction On-Water
    Daniel J. Eyckens
    Hannah L. Brozinski
    Joshua P. Delaney
    Linden Servinis
    Sahar Naghashian
    Luke C. Henderson
    Catalysis Letters, 2016, 146 : 212 - 219
  • [39] Asymmetric Aldol Reaction of Dichloroacetaldehyde Catalyzed by Diarylprolinol
    Hayashi, Yujiro
    Nakamura, Daichi
    Yasui, Yusuke
    Iwasaki, Kotaro
    Chiba, Hiroaki
    ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (14) : 2345 - 2351
  • [40] Asymmetric Aldol Reaction of Chloral Catalyzed by Diarylprolinol
    Hayashi, Yujiro
    Watanabe, Shoya
    Yasui, Yusuke
    Umemiya, Shigenobu
    CHEMCATCHEM, 2015, 7 (11) : 1646 - 1649
12345