Highly efficient direct large-scale stoichiometric aldol reactions catalyzed by a new diamine salt in the presence of water

被引:4
|
作者
Huang, Jing [1 ]
Chen, Guodong [1 ]
Fu, Xiangkai [1 ]
Li, Chao [1 ]
Wu, Chuanlong [1 ]
Miao, Qiang [1 ]
机构
[1] Southwest Univ, Key Lab Appl Chem Chongqing Municipal, Key Lab Ecoenvironm Three Gorges Reservoir Reg, Coll Chem & Chem Engn,Res Inst Appl Chem,Minist E, Chongqing 400715, Peoples R China
关键词
ORGANIC-REACTIONS; L-PROLINAMIDE; BIFUNCTIONAL ORGANOCATALYSTS; AMINE ORGANOCATALYSTS; N-PROLYLSULFONAMIDE; CYCLIC-KETONES; ACID; DERIVATIVES; MICHAEL; DESIGN;
D O I
10.1039/c1cy00318f
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
A new type of primary-tertiary diamine salt prepared can be used as a catalyst for direct aldol reaction and can display high yields, diastereoselectivities (up to 99 : 1), and enantiomeric excesses (up to 98%), by using stoichiometric amounts of cyclic ketones and various aryl aldehydes in the presence of water. This new catalyst can also be efficiently applied in large-scale reactions with the enantioselectivity being maintained at the same level, which indicates the potential for applications in industry.
引用
收藏
页码:547 / 553
页数:7
相关论文
共 41 条
  • [1] Highly efficient asymmetric direct stoichiometric aldol reactions on/in water
    Huang, Junmin
    Zhang, Xiaotong
    Armstrong, Daniel W.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (47) : 9073 - 9077
  • [2] Highly stereoselective direct aldol reactions catalyzed by a bifunctional chiral diamine
    Li, Lei
    Gou, Shaohua
    Liu, Fei
    TETRAHEDRON-ASYMMETRY, 2014, 25 (02) : 193 - 197
  • [3] A Highly Efficient, Large-Scale, Asymmetric Direct Aldol Reaction Employing Simple Threonine Derivatives as Recoverable Organocatalysts in the Presence of Water
    Wu, Chuanlong
    Fu, Xiangkai
    Li, Shi
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (07) : 1291 - 1299
  • [4] Simple and inexpensive threonine-based organocatalysts as highly active and recoverable catalysts for large-scale asymmetric direct stoichiometric aldol reactions on water
    Wu, Chuanlong
    Long, Xiaoqin
    Li, Shi
    Fu, Xiangkai
    TETRAHEDRON-ASYMMETRY, 2012, 23 (05) : 315 - 328
  • [5] 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
  • [6] Simple proline derivatives as recoverable catalysts for the large-scale stoichiometric aldol reactions
    Li, Shi
    Wu, Chuanlong
    Long, Xiaoqin
    Fu, Xiangkai
    Chen, Guodong
    Liu, Zhijian
    CATALYSIS SCIENCE & TECHNOLOGY, 2012, 2 (05) : 1068 - 1071
  • [7] Dipeptide-catalyzed direct asymmetric aldol reactions in the presence of water
    Lei, Meng
    Shi, Lanxiang
    Li, Gong
    Chen, Shilv
    Fang, Weihai
    Ge, Zemei
    Cheng, Tieming
    Li, Runtao
    TETRAHEDRON, 2007, 63 (33) : 7892 - 7898
  • [8] Highly efficient direct a larger-scale aldol reactions catalyzed by a flexible prolinamide based-metal Lewis acid bifunctional catalyst in the presence of water
    Chen, Guodong
    Fu, Xiangkai
    Li, Chao
    Wu, Chuanlong
    Miao, Qiang
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2012, 702 : 19 - 26
  • [9] Highly diastereo- and enantioselective direct aldol reactions of aldehydes and ketones catalyzed by siloxyproline in the presence of water
    Aratake, Seiji
    Itoh, Takahiko
    Okano, Tsubasa
    Nagae, Norio
    Sumiya, Tatsunobu
    Shoji, Mitsuru
    Hayashi, Yujiro
    CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (36) : 10246 - 10256
  • [10] Simple, inexpensive, and facile L-prolinamide used as a recyclable organocatalyst for highly efficient large-scale asymmetric direct aldol reactions
    Xu, Jiangwei
    Fu, Xiangkai
    Wu, Chuanlong
    Hu, Xiaoyan
    TETRAHEDRON-ASYMMETRY, 2011, 22 (08) : 840 - 850