Dipeptide-catalyzed direct asymmetric aldol reaction

被引:82
|
作者
Shi, LX [1 ]
Sun, Q [1 ]
Ge, ZM [1 ]
Zhu, YQ [1 ]
Cheng, TM [1 ]
Li, RT [1 ]
机构
[1] Peking Univ, Sch Pharmaceut Sci, Beijing 100083, Peoples R China
关键词
aldol reaction; organocatalysis; enamine catalysis; dipeptides;
D O I
10.1055/s-2004-831324
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
(L)-H-Pro-(L)-Phe-OH (4) were found to be efficient catalysts for direct asymmetric aldol reactions between acetone and various aldehydes. The reaction conditions use a DMSO-NMM-PEMG 5000 system at 0 degreesC in high yields (62-96%) and enantioselectivities (up to >99% ee).
引用
收藏
页码:2215 / 2217
页数:3
相关论文
共 50 条
  • [31] Progress in the study on the reaction mechanisms of proline-catalyzed asymmetric direct aldol reactions
    Fan, Jian-Fen
    Sun, Yun-Peng
    Xiao, He-Ming
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2006, 26 (11) : 1463 - 1467
  • [32] Asymmetric direct aldol reaction of functionalized ketones catalyzed by amine organocatalysts based on bispidine
    Key Laboratory of Green Chemistry and Technology , College of Chemistry, Sichuan University, Chengdu 610064, China
    不详
    J. Am. Chem. Soc., 2008, 17 (5654-5655):
  • [33] L-t-Leucine-Catalyzed Direct Asymmetric Aldol Reaction of Cyclic Ketones
    Kanemitsu, Takuya
    Umehara, Atsushi
    Miyazaki, Michiko
    Nagata, Kazuhiro
    Itoh, Takashi
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (05) : 993 - 997
  • [34] Asymmetric direct aldol reaction of functionalized ketones catalyzed by amine organocatalysts based on bispidine
    Liu, Jie
    Yang, Zhigang
    Wang, Zhen
    Wang, Fei
    Chen, Xiaohong
    Liu, Xiaohua
    Feng, Xiaoming
    Su, Zhishan
    Hu, Changwei
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (17) : 5654 - +
  • [35] Direct Catalytic Asymmetric Aldol Reaction of α-Alkylamides
    Liu, Zijian
    Takeuchi, Toshifumi
    Pluta, Roman
    Arteaga, Fernando Arteaga
    Kumagai, Naoya
    Shibasaki, Masakatsu
    ORGANIC LETTERS, 2017, 19 (03) : 710 - 713
  • [36] Novel Ureas Based on Dipeptide Analogues as Organocatalysts for the Asymmetric Aldol Reaction
    Revelou, P.
    Kokotos, C. G.
    Moutevelis-Mlnakakis, P.
    JOURNAL OF PEPTIDE SCIENCE, 2012, 18 : S113 - S113
  • [37] Redox Tuning of a Direct Asymmetric Aldol Reaction
    Zhang, Qiying
    Cui, Xiuling
    Zhang, Long
    Luo, Sanzhong
    Wang, Hui
    Wu, Yangjie
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (17) : 5210 - 5213
  • [38] Direct asymmetric Aldol-Tishchenko reaction
    Mlynarski, Jacek
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (21) : 4779 - 4786
  • [39] Proline-catalyzed direct asymmetric aldol reactions
    1600, ACS, Washington, DC, USA (122):
  • [40] Proline-catalyzed direct asymmetric aldol reactions
    List, B
    Lerner, RA
    Barbas, CF
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (10) : 2395 - 2396