Highly Enantioselective Co-Catalytic Direct Aldol Reactions by Combination of Hydrogen-Bond Donating and Acyclic Amino Acid Catalysts

被引：38
作者：
Ma, Guangning [1 ]
Bartoszewicz, Agnieszka [2 ,3 ]
Ibrahem, Ismail [1 ]
Cordova, Armando [1 ,2 ,3 ]
机构：
[1] Mid Sweden Univ, Dept Nat Sci Engn & Math, SE-85170 Sundsvall, Sweden
[2] Stockholm Univ, Arrhenius Lab, Dept Organ Chem, SE-10691 Stockholm, Sweden
[3] Stockholm Univ, Berzelii Ctr EXSELENT, SE-10691 Stockholm, Sweden
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2011年 / 353卷 / 17期
关键词：
aldol reaction; amino acids; asymmetric catalysis; co-catalysis; hydrogen-bond donating; UNMODIFIED ALPHA; BETA-UNSATURATED ALDEHYDES; HILLMAN-TYPE REACTIONS; DIELS-ALDER REACTION; ASYMMETRIC-SYNTHESIS; TRANSITION-METAL; SUPRAMOLECULAR CHEMISTRY; ALPHA-ACYLOXYACROLEINS; ADDITION-REACTIONS; ENAMINE CATALYSIS; MICHAEL ADDITION;
D O I：
10.1002/adsc.201100408
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
Highly enantioselective co-catalytic direct aldol reactions by a combination of simple hydrophobic acyclic amino acid and hydrogen-bond donating catalysts are presented. The corresponding aldol products are formed in high yields with high regio-, diastereo-(anti or syn) and enantioselectivity (up to 99.5:0.5 er). The catalyst loadings can be decreased to as little as 2 mol%.
引用
收藏
页码：3114 / 3122
页数：9
相关论文
共 13 条
  • [1] Proline-derived N-sullfonylcarboxamides:: Readily available, highly enantioselective and versatile catalysts for direct aldol reactions
    Berkessel, A
    Koch, B
    Lex, J
    ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (9-10) : 1141 - 1146
  • [2] Dynamic One-Pot Three-Component Catalytic Asymmetric Transformation by Combination of Hydrogen-Bond-Donating and Amine Catalysts
    Lin, Shuangzheng
    Deiana, Luca
    Zhao, Gui-Ling
    Sun, Junliang
    Cordova, Armando
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (33) : 7624 - 7630
  • [3] Exploiting β-Amino Acid Enolates in Direct Catalytic Diastereo- and Enantioselective C-C Bond-Forming Reactions
    Yu, Jin-Sheng
    Noda, Hidetoshi
    Shibasaki, Masakatsu
    CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (59) : 15796 - 15800
  • [4] An efficient method for direct aldol reactions catalyzed by pyrrolidine/catechol - The influence of cooperation of Bronsted acidity and hydrogen-bond on the reaction
    Ji, CY
    Peng, YG
    Huang, CZ
    Wang, N
    Luo, Z
    Jiang, YZ
    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2006, 246 (1-2) : 136 - 139
  • [5] Chiral Catalysts Dually Functionalized with Amino Acid and Zn2+ Complex Components for Enantioselective Direct Aldol Reactions Inspired by Natural Aldolases: Design, Synthesis, Complexation Properties, Catalytic Activities, and Mechanistic Study
    Itoh, Susumu
    Kitamura, Masanori
    Yamada, Yasuyuki
    Aoki, Shin
    CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (40) : 10570 - 10584
  • [6] Highly enantioselective direct syn- and anti-aldol reactions of dihydroxyacetones catalyzed by chiral primary amine catalysts
    Luo, Sanzhong
    Xu, Hui
    Zhang, Long
    Li, Jiuyuan
    Cheng, Jin-Pei
    ORGANIC LETTERS, 2008, 10 (04) : 653 - 656
  • [7] Achiral Co-Catalyst Induced Switches in Catalytic Asymmetric Reactions on Racemic Mixtures (RRM): From Stereodivergent RRM to Stereoconvergent Deracemization by Combination of Hydrogen Bond Donating and Chiral Amine Catalysts
    Ma, Guangning
    Lin, Shuangzheng
    Ibrahem, Ismail
    Kubik, Grzegorz
    Liu, Leifeng
    Sun, Junliang
    Cordova, Armando
    ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (14-15) : 2865 - 2872
  • [8] Development of an Amino Acid/Hydroxy Oxime Dual Catalyst System for Highly Stereoselective Direct Asymmetric Aldol Reactions in the Presence of Water
    Mridha, Moniruzzaman
    Ma, Guangning
    Palo-Nieto, Carlos
    Afewerki, Samson
    Cordova, Armando
    SYNTHESIS-STUTTGART, 2017, 49 (02): : 383 - 390
  • [9] New simple and recyclable O-acylation serine derivatives as highly enantioselective catalysts for the large-scale asymmetric direct aldol reactions in the presence of water
    Wu, Chuanlong
    Fu, Xiangkai
    Li, Shi
    TETRAHEDRON, 2011, 67 (23) : 4283 - 4290
  • [10] The direct catalytic asymmetric cross-Mannich reaction:: A highly enantioselective route to 3-amino alcohols and α-amino acid derivatives
    Córdova, A
    CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (08) : 1987 - 1997
12