Proline-based dipeptides as efficient organocatalysts for asymmetric aldol reactions in brine

被引：21
|
作者：
Tian, Hua [2 ]
Gao, Jun-long [2 ]
Xu, Hao [2 ]
Zheng, Liang-Yu [1 ]
Huang, Wen-Bo [2 ]
Liu, Qing-Wen [2 ]
Zhang, Suo-Qin
机构：
[1] Jilin Univ, Minist Educ, Key Lab Mol Enzymol & Engn, Changchun 130012, Peoples R China
[2] Jilin Univ, Coll Chem, Changchun 130012, Peoples R China
来源：
TETRAHEDRON-ASYMMETRY | 2011年 / 22卷 / 10期
基金：
中国国家自然科学基金;
关键词：
HIGHLY EFFICIENT; N-PROLYLSULFONAMIDE; ENAMINE CATALYSIS; WATER; ALDEHYDES; KETONES; DIHYDROXYACETONE; CYCLOHEXANONE; DERIVATIVES; DESIGN;
D O I：
10.1016/j.tetasy.2011.06.017
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Simple N-proline-based dipeptides with two N-H groups in combination with 2,4-dinitrophenol (DNP) catalyze the direct asymmetric aldol reactions of aldehydes with a broad range of ketones to furnish the corresponding aldol products in high yields (up to 99%) and with high enantioselectivities (up to 97%) and diastereoselectivities (up to > 99:1, anti/syn) at room temperature and in brine. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1074 / 1080
页数：7
相关论文
共 50 条
  • [1] Proline-based Amino Pyridine Dipeptides as Efficient Organocatalysts for Direct Aldol Reaction
    GAO Jun-long1
    [J]. Chemical Research in Chinese Universities, 2010, 26 (01) : 50 - 54
  • [2] Proline-based Amino Pyridine Dipeptides as Efficient Organocatalysts for Direct Aldol Reaction
    Gao Jun-long
    Zheng Liang-yu
    Zhang Suo-qin
    Zhang Xin-min
    Sun Guo-dong
    Qin Lin
    Li Yao-xian
    Liu Qing-wen
    Li Xiao-bo
    [J]. CHEMICAL RESEARCH IN CHINESE UNIVERSITIES, 2010, 26 (01) : 50 - 54
  • [3] Polymer Supported Proline-Based Organocatalysts in Asymmetric Aldol Reactions: A Review
    Shajahan, Rubina
    Sarang, Rithwik
    Saithalavi, Anas
    [J]. CURRENT ORGANOCATALYSIS, 2022, 9 (02) : 124 - 146
  • [4] Proline-based reduced dipeptides as recyclable and highly enantioselective organocatalysts for asymmetric Michael addition
    Cao, Xiaohui
    Wang, Ge
    Zhang, Richeng
    Wei, Yingying
    Wang, Wei
    Sun, Huichao
    Chen, Ligong
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (19) : 6487 - 6490
  • [5] Novel chiral proline-based organocatalysts with amide and thiourea-amine units for highly efficient asymmetric aldol reaction in saturated brine without additives
    Xu, En-Jie
    Song, Yan
    Wei, Zhong-Lin
    Wang, Rui
    Duan, Hai-Feng
    Lin, Ying-Jie
    Yang, Qing-Biao
    Li, Yao-Xian
    [J]. CANADIAN JOURNAL OF CHEMISTRY, 2019, 97 (05) : 352 - 359
  • [6] Asymmetric Aldol Reactions Catalyzed by Efficient and Recyclable Silica-Supported Proline-Based Peptides
    Yan, Jincan
    Wang, Lei
    [J]. CHIRALITY, 2009, 21 (04) : 413 - 420
  • [7] Proline-based dipeptides with two amide units as organocatalyst for the asymmetric aldol reaction of cyclohexanone with aldehydes
    Chen, Fubin
    Huang, Shi
    Zhang, Hui
    Liu, Fengying
    Peng, Yungui
    [J]. TETRAHEDRON, 2008, 64 (40) : 9585 - 9591
  • [8] Proline-Based Polymeric Monoliths: Synthesis, Characterization, and Applications as Organocatalysts in Aldol Reaction
    Garg, Dipti
    Ahn, J. -H
    Chauhan, Ghanshyam S.
    [J]. JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2010, 48 (05) : 1007 - 1015
  • [9] Direct asymmetric aldol reactions in brine with recyclable fluorous β-aminosulfonamide organocatalysts
    Miura, Tsuyoshi
    Imai, Kie
    Kasuga, Hikaru
    Ina, Mariko
    Tada, Norihiro
    Imai, Nobuyuki
    Itoh, Akichika
    [J]. TETRAHEDRON, 2011, 67 (34) : 6340 - 6346
  • [10] Highly efficient prollinamide-based organocatalysts for the direct asymmetric aldol reaction in brine
    Jia, Ya-Ning
    Wu, Feng-Chun
    Ma, Xiao
    Zhu, Gong-Jian
    Da, Chao-Shan
    [J]. TETRAHEDRON LETTERS, 2009, 50 (25) : 3059 - 3062
12345