Asymmetric direct aldol reaction assisted by water and a proline-derived tetrazole catalyst

被引：555
|
作者：
Torii, H
Nakadai, M
Ishihara, K
Saito, S [1 ]
Yamamoto, H
机构：
[1] Nagoya Univ, Inst Adv Res, Nagoya, Aichi 4648602, Japan
[2] Nagoya Univ, Grad Sch Sci, Nagoya, Aichi 4648602, Japan
[3] Univ Chicago, Dept Chem, Chicago, IL 60637 USA
[4] Nagoya Univ, Grad Sch Engn, Nagoya, Aichi 4648603, Japan
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2004年 / 43卷 / 15期
关键词：
aldol reaction; amines; asymmetric catalysis; tetrazole; water;
D O I：
10.1002/anie.200352724
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Just add water to improve the performance of direct aldol reactions like that shown. Previously, aldehydes with high water-affinity or -solubility were considered unsuitable for asymmetric synthesis.
引用
收藏
页码：1983 / 1986
页数：4
相关论文
共 50 条
  • [41] Exploring "Through-Bond" Proximity between the Ion Tag and Reaction Site of an Imidazolium-Proline Catalyst for the Direct Asymmetric Aldol Reaction
    Bhati, Meeta
    Upadhyay, Shruti
    Easwar, Srinivasan
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (13) : 1788 - 1793
  • [42] L-proline/cholesterol and diosgenin based thiourea cooperative system for the direct asymmetric aldol reaction in the presence of water
    Eymur, Serkan
    Tasci, Enis
    Uyanik, Arzu
    Yilmaz, Mustafa
    TURKISH JOURNAL OF CHEMISTRY, 2020, 44 (05) : 1278 - +
  • [43] Direct catalytic asymmetric aldol reaction
    Yoshikawa, N
    Yamada, YMA
    Das, J
    Sasai, H
    Shibasaki, M
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (17) : 4168 - 4178
  • [44] The direct catalytic asymmetric aldol reaction
    Trost, Barry M.
    Brindle, Cheyenne S.
    CHEMICAL SOCIETY REVIEWS, 2010, 39 (05) : 1600 - 1632
  • [45] The direct catalytic asymmetric aldol reaction
    Alcaide, B
    Almendros, P
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2002, 2002 (10) : 1595 - 1601
  • [46] Proline-modified DNA as catalyst of the aldol reaction
    Tang, Zhuo
    Marx, Andreas
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (38) : 7297 - 7300
  • [47] Pentafluorophenyl-Substituted Proline-Derived Chiral Urea for "On Water" Asymmetric Hydrogen-Bonding Catalysis
    Wang, Bingfu
    Li, Tianxing
    Liu, Jian
    Wang, Shuo
    Shi, Hu
    Jin, Hui
    Ryu, Do Hyun
    Zhang, Lixin
    ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (23) : 4155 - 4162
  • [48] Recyclable Merrifield resin-supported thiourea organocatalysts derived from L-proline for direct asymmetric aldol reaction
    Li, Jia
    Yang, Gengxu
    Qin, Yanyan
    Yang, Xinran
    Cui, Yuanchen
    TETRAHEDRON-ASYMMETRY, 2011, 22 (06) : 613 - 618
  • [49] Rationally designed organocatalyst for direct asymmetric aldol reaction in the presence of water
    Wang, Chao
    Jiang, Yi
    Zhang, Xiao-xia
    Huang, Yi
    Li, Bo-gang
    Zhang, Guo-lin
    TETRAHEDRON LETTERS, 2007, 48 (24) : 4281 - 4285
  • [50] The small peptide-catalyzed direct asymmetric aldol reaction in water
    Dziedzic, P
    Zou, WB
    Háfren, J
    Córdova, A
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (01) : 38 - 40
12345