Organo-catalyzed highly diastereo- and enantio-selective direct aldol reactions in water

被引:72
|
作者
Zhao, Jun-Feng [1 ,2 ,3 ]
He, Long [4 ,5 ]
Jiang, Jun [1 ,2 ,3 ]
Tang, Zhuo [1 ,2 ,3 ]
Cun, Lin-Feng [1 ,2 ,3 ]
Gong, Liu-Zhu [1 ,2 ,3 ,4 ,5 ]
机构
[1] Chinese Acad Sci, Key Lab Asymmetr Synthesis & Chirotechnol Sichuan, Chengdu 610041, Peoples R China
[2] Chinese Acad Sci, Union Lab Asymmetr Synthesis, Chengdu 610041, Peoples R China
[3] Chinese Acad Sci, Grad Sch, Beijing, Peoples R China
[4] Hefei Natl Lab Phys Sci Microscale, Hefei 230026, Peoples R China
[5] Dept Chem Sci & Technol China, Hefei 230026, Peoples R China
基金
中国国家自然科学基金;
关键词
water; organocatalysis; direct aldol; diastereo- and enantio-selective;
D O I
10.1016/j.tetlet.2008.03.131
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The asymmetric direct aldol reactions of a wide scope of aromatic aldehydes, with unmodified ketones in the presence of 1 mol % of organocatalyst prepared from (2R,3R)-diethyl 2-amino-3-hydroxysuccinate and trans-4-hydroxy-L-proline, were performed in water, affording aldol products in high yields with excellent diastereoselectivities of up to >99:1 and enantioselectivities of up to 98%. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3372 / 3375
页数:4
相关论文
共 50 条
  • [11] L-Proline/CoCl2-Catalyzed Highly Diastereo- and Enantioselective Direct Aldol Reactions
    Karmakar, Ananta
    Maji, Tapan
    Wittmann, Sebastian
    Reiser, Oliver
    CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (39) : 11024 - 11029
  • [12] Diastereo- and enantio-selective crotylation of α-ketoesters using crotyl boronic acid ester complexes
    Chen, YP
    Eltepu, L
    Wentworth, P
    TETRAHEDRON LETTERS, 2004, 45 (45) : 8285 - 8288
  • [13] Highly Diastereo- and Enantioselective Direct Aldol Reaction Catalyzed by Simple Amphiphilic Proline Derivatives
    Yu-Qin Fu
    Ya-Jie An
    Wei-Min Liu
    Zai-Chun Li
    Gen Zhang
    Jing-Chao Tao
    Catalysis Letters, 2008, 124 : 397 - 404
  • [14] Highly diastereo- and enantioselective direct aldol reaction catalyzed by simple amphiphilic proline derivatives
    Fu, Yu-Qin
    An, Ya-Jie
    Liu, Wei-Min
    Li, Zai-Chun
    Zhang, Gen
    Tao, Jing-Chao
    CATALYSIS LETTERS, 2008, 124 (3-4) : 397 - 404
  • [15] Highly diastereo- and enantioselective direct Barbas-List aldol reactions promoted by novel benzamidoethyl and benzamidopropyl prolinamides in water
    Pedrosa, Rafael
    Andres, Jose M.
    Manzano, Ruben
    Roman, David
    Tellez, Silvia
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (03) : 935 - 940
  • [16] Picolylamine as an organocatalyst template for highly diastereo- and enantioselective aqueous aldol reactions
    Nugent, Thomas C.
    Umar, M. Naveed
    Bibi, Ahtaram
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (18) : 4085 - 4089
  • [17] DIASTEREO-SELECTIVE AS WELL AS ENANTIO-SELECTIVE LIPASE-CATALYZED ASYMMETRIC HYDROLYSIS OF CHLOROFLUOROMETHYLATED ALCOHOLS
    YAMAZAKI, T
    ICHIKAWA, S
    KITAZUME, T
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (04) : 253 - 255
  • [18] Diastereo- and enantio-selective synthesis of 6-heterosubstituted-3,5-dihydroxyesters: Novel precursors of mevinolin analogues
    Enders, D
    Burkamp, F
    Runsink, J
    CHEMICAL COMMUNICATIONS, 1996, (05) : 609 - 610
  • [19] Highly diastereo- and enantioselective direct aldol reactions of cycloketones with aldehydes catalyzed by a trans-4-tert-butyldimethylsiloxy-L-proline amide
    He, Long
    Jiang, Jun
    Tang, Zhuo
    Cui, Xin
    Mi, Ai-Qiao
    Jiang, Yao-Zhong
    Gong, Liu-Zhu
    TETRAHEDRON-ASYMMETRY, 2007, 18 (02) : 265 - 270
  • [20] Highly Diastereo- and Enantioselective Direct Aldol Reactions Promoted by Water-Compatible Organocatalysts Bearing Central and Axial Chiral Elements
    Peng, Fang-Zhi
    Shao, Zhi-Hui
    Pu, Xue-Wei
    Zhang, Hong-Bin
    ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (14-15) : 2199 - 2204