Water-soluble calixarenes as new inverse phase-transfer catalysts. Their application to aldol-type condensation and Michael addition reactions in water

被引：54
|
作者：
Shimizu, S [1 ]
Shirakawa, S
Suzuki, T
Sasaki, Y
机构：
[1] Nihon Univ, Dept Appl Mol Chem, Narashino, Chiba 2758575, Japan
[2] Nihon Univ, Coll Ind Technol, High Technol Res Ctr, Narashino, Chiba 2758575, Japan
来源：
TETRAHEDRON | 2001年 / 57卷 / 29期
关键词：
calixarenes; catalysis; water; aldol reactions;
D O I：
10.1016/S0040-4020(01)00572-5
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Aldol-type condensation and Michael addition reactions of activated methyl and methylene compounds in aqueous NaOH solution have been developed without the need for any added organic solvents. The water-soluble calix[n]arenes, which contain trimethyl-ammoniomethyl groups on the upper rim, were used as inverse phase-transfer catalysts, resulting in the corresponding products in good to excellent yields. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：6169 / 6173
页数：5
相关论文
共 11 条
  • [1] Water-soluble calixarenes as new inverse phase-transfer catalysts.: Their application to C-alkylations of active methylene compounds in water
    Shimizu, S
    Suzuki, T
    Sasaki, Y
    Hirai, C
    SYNLETT, 2000, (11) : 1664 - 1666
  • [2] Water-soluble calixarenes as new inverse phase-transfer catalysts. Their scope in aqueous biphasic Alkylations and mechanistic implications
    Shimizu, S
    Suzuki, T
    Shirakawa, S
    Sasaki, Y
    Hirai, C
    ADVANCED SYNTHESIS & CATALYSIS, 2002, 344 (3-4) : 370 - 378
  • [3] Water-soluble calixarenes as new inverse phase-transfer catalysts. Nucleophilic substitution of alkyl and arylalkyl halides in aqueous media
    Shimizu, S
    Kito, K
    Sasaki, Y
    Hirai, C
    CHEMICAL COMMUNICATIONS, 1997, (17) : 1629 - 1630
  • [4] Mannich-type reactions in water using anionic water-soluble calixarenes as recoverable and reusable catalysts
    Shimizu, Shoichi
    Shimada, Naoyuki
    Sasaki, Yasuyuki
    GREEN CHEMISTRY, 2006, 8 (07) : 608 - 614
  • [5] Highly Enantioselective Asymmetric Michael Addition Reactions with New Chiral Multisite Phase-Transfer Catalysts
    Jayaraman, Sivamani
    Kumaraguru, Duraimurugan
    Arockiam, Jesin Beneto
    Paulpandian, Subha
    Rajendiran, Balasaravanan
    Siva, Ayyanar
    SYNLETT, 2014, 25 (12) : 1685 - 1691
  • [6] Michael Condensation in a Two-Phase System: The Application of Inverse Phase-Transfer Catalysis to the Reaction of Butyl Acrylate with Diethylamine in a Water–Heptane System
    G. S. Simonyan
    N. M. Beileryan
    Kinetics and Catalysis, 2002, 43 : 337 - 340
  • [7] TRIS(PENTAFLUOROPHENYL)BORON AS A NEW EFFICIENT, AIR-STABLE, AND WATER TOLERANT CATALYST IN THE ALDOL-TYPE AND MICHAEL REACTIONS
    ISHIHARA, K
    HANANKI, N
    YAMAMOTO, H
    SYNLETT, 1993, (08) : 577 - 579
  • [8] Michael condensation in a two-phase system: The application of inverse phase-transfer catalysis to the reaction of butyl acrylate with diethylamine in a water-heptane system
    Simonyan, GS
    Beileryan, NM
    KINETICS AND CATALYSIS, 2002, 43 (03) : 337 - 340
  • [9] Syntheses of water-soluble N-donor ligands for aqueous catalysis using green, Michael-type addition reactions
    Liang, HC
    Das, SK
    Galvan, JR
    Sato, SM
    Zhang, YL
    Zakharov, LN
    Rheingold, AL
    GREEN CHEMISTRY, 2005, 7 (06) : 410 - 412
  • [10] Water-soluble calix[n]arenes as receptor molecules for non-polar substrates and inverse phase transfer catalysts
    Baur, M
    Frank, M
    Schatz, J
    Schildbach, F
    TETRAHEDRON, 2001, 57 (32) : 6985 - 6991
12