Desymmetrisation of meso-diones promoted by a highly recyclable polymer-supported chiral phosphoric acid catalyst

被引：14
|
作者：
Clot-Almenara, Lidia [1 ]
Rodriguez-Escrich, Carles [1 ]
Pericas, Miquel A. [1 ,2 ]
机构：
[1] Barcelona Inst Sci & Technol, Inst Chem Res Catalonia ICIQ, Av Paisos Catalans 16, Tarragona 43007, Spain
[2] Univ Barcelona, Dept Quim Inorgan & Organ, Barcelona 08080, Spain
来源：
RSC ADVANCES | 2018年 / 8卷 / 13期
关键词：
SAUER-WIECHERT REACTION; BRONSTED ACID; ASYMMETRIC-SYNTHESIS; WIELAND-MIESCHER; CONTINUOUS-FLOW; ALDOL REACTIONS; PROLINE-DERIVATIVES; ORGANIC CATALYSTS; ENAMINE CATALYSIS; PRIMARY AMINE;
D O I：
10.1039/c7ra13471a
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A polystyrene-supported BINOL-derived chiral phosphoric acid has been applied to the desymmetrisation of meso-diones to produce enantioenriched cyclohexenones. The catalytic resin has proven highly active and robust, giving rise to Hajos-Parrish or Wieland-Miescher type products in good yields and enantioselectivities, while allowing for extended recycling.
引用
收藏
页码：6910 / 6914
页数：5
相关论文
共 50 条
  • [11] Polymer-Supported Chiral-at-Metal Lewis Acid Catalysts
    Larionov, Vladimir A.
    Cruchter, Thomas
    Mietke, Thomas
    Meggers, Eric
    [J]. ORGANOMETALLICS, 2017, 36 (08) : 1457 - 1460
  • [12] Synthesis and Application of Polymer-Supported Chiral Bronsted Acid Organocatalysts
    Rueping, Magnus
    Sugiono, Erli
    Steck, Alexander
    Theissmann, Thomas
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (2-3) : 281 - 287
  • [13] Chiral Phosphoric Acid Catalyzed Desymmetrization of meso-1,3-Diones: Asymmetric Synthesis of Chiral Cyclohexenones
    Mori, Keiji
    Katoh, Takuya
    Suzuki, Tohru
    Noji, Takuya
    Yamanaka, Masahiro
    Akiyama, Takahiko
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (51) : 9652 - 9654
  • [14] Enantioselective Strecker-type reaction promoted by polymer-supported bifunctional catalyst
    Nogami, H
    Matsunaga, S
    Kanai, M
    Shibasaki, M
    [J]. TETRAHEDRON LETTERS, 2001, 42 (02) : 279 - 283
  • [15] Polymer-Supported Cu–Nanoparticle as an Efficient and Recyclable Catalyst for Oxidative Homocoupling of Terminal Alkynes
    Sk Tarik Aziz
    Rafique Ul Islam
    [J]. Catalysis Letters, 2018, 148 : 205 - 213
  • [16] Polymer-supported azidoproazaphosphatrane: A recyclable catalyst for the room-temperature transformation of triglycerides to biodiesel
    Reddy, Chinta Reddy Venkat
    Fetterly, Brandon M.
    Verkade, John G.
    [J]. ENERGY & FUELS, 2007, 21 (04) : 2466 - 2472
  • [17] Polymer-supported ytterbium perfluorooctanesulfonate [Yb(OPf)3]:: A recyclable catalyst for organic reactions
    Yi, Wen-Bin
    Cai, Chun
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 2008, 129 (06) : 524 - 528
  • [18] One-pot synthesis of aniline derivatives from nitroarenes under mild conditions promoted by a recyclable polymer-supported palladium catalyst
    Dell'Anna, Maria Michela
    Mastrorilli, Piero
    Rizzuti, Antonino
    Leonelli, Cristina
    [J]. APPLIED CATALYSIS A-GENERAL, 2011, 401 (1-2) : 134 - 140
  • [19] Design of novel polymer-supported chiral catalyst for asymmetric transfer hydrogenation in water
    Arakawa, Y
    Haraguchi, N
    Itsuno, S
    [J]. TETRAHEDRON LETTERS, 2006, 47 (19) : 3239 - 3243
  • [20] Photocatalytic Aerobic Oxidation of Alkenes into Epoxides or Chlorohydrins Promoted by a Polymer-Supported Decatungstate Catalyst
    Symeonidis, Theodoros S.
    Athanasoulis, Alexandros
    Ishii, Rikako
    Uozumi, Yasuhiro
    Yamada, Yoichi M. A.
    Lykakis, Ioannis N.
    [J]. CHEMPHOTOCHEM, 2017, 1 (10): : 479 - 484
12345