General and versatile synthesis of highly recyclable chiral phosphoric acid organocatalysts

被引:0
|
作者
Maestro, Aitor [1 ,2 ]
Oetvoes, Sandor B. [2 ,3 ]
Auer, Gerald [4 ]
Kappe, C. Oliver [2 ,3 ]
机构
[1] Univ Basque Country UPV EHU, Dept Organ Chem 1, Paseo Univ 7, Vitoria 01006, Spain
[2] Karl Franzens Univ Graz, Inst Chem, NAWI Graz, A-8010 Graz, Austria
[3] Res Ctr Pharmaceut Engn GmbH RCPE, Ctr Continuous Flow Synth & Proc CC Flow, A-8010 Graz, Austria
[4] Karl Franzens Univ Graz, Dept Earth Sci, NAWI Graz Geoctr, A-8010 Graz, Austria
基金
奥地利科学基金会;
关键词
CATALYTIC ASYMMETRIC-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; DIHYDROQUINAZOLINONES; LIGANDS;
D O I
10.1039/d4qo01442a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The development of recyclable catalysts has gained more attention in recent years in order to minimize the environmental effect and the overall cost of catalytic processes. Some of the most broadly used chiral organocatalysts are BINOL-derived chiral phosphoric acids, making it necessary to develop efficient recycling strategies. While literature reports require up to 13 synthetic steps to access recyclable chiral phosphoric acids, here we report a general and concise 9-step approach to anthracene decorated heterogeneous chiral phosphoric acids (PS-Anth), which have shown high performance either in batch or continuous flow without observing catalyst degradation. We report a general and concise 9-step approach to heterogeneous chiral phosphoric acids and their application as highly recyclable organocatalysts in batch and continuous flow.
引用
收藏
页数:7
相关论文
共 50 条
  • [21] Applications of chiral spirocyclic phosphoric acid in the synthesis of natural products
    Yang, Fan
    [J]. 2021 5TH INTERNATIONAL CONFERENCE ON ADVANCES IN ENERGY, ENVIRONMENT AND CHEMICAL SCIENCE (AEECS 2021), 2021, 245
  • [22] Chiral Phosphoric Acids as Versatile Catalysts for Enantioselective Transformations
    Terada, Masahiro
    [J]. SYNTHESIS-STUTTGART, 2010, (12): : 1929 - 1982
  • [23] Synthesis of a biphenyl-based phosphoric acid for chiral Bronsted acid catalysis
    Gutierrez, Elisa G.
    Ackerman, Laura K. G.
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 237
  • [24] S-chiral sulfinamides as highly enantioselective organocatalysts
    Pei, Dong
    Wang, Zhouyu
    Wei, Siyu
    Zhang, Yu
    Sun, Jian
    [J]. ORGANIC LETTERS, 2006, 8 (25) : 5913 - 5915
  • [25] Highly Practical Amino Acid and Alkaloid Synthesis Using Designer Chiral Phase Transfer Catalysts as High-Performance Organocatalysts
    Maruoka, Keiji
    [J]. CHEMICAL RECORD, 2010, 10 (05): : 254 - 259
  • [26] Pyrrolidine-based chiral pyridinium ionic liquids (ILs) as recyclable and highly efficient organocatalysts for the asymmetric Michael addition reactions
    Ni, Bukuo
    Zhang, Qianying
    Headley, Allan D.
    [J]. TETRAHEDRON LETTERS, 2008, 49 (07) : 1249 - 1252
  • [27] Design of Planar Chiral Phosphoric Acids with a [2.2]Paracyclophanyl Backbone as Organocatalysts for the Highly Enantioselective Aza-Friedel-Crafts Reaction
    Xie, En
    Huang, Shaoying
    Lin, Xufeng
    [J]. ORGANIC LETTERS, 2019, 21 (10) : 3682 - 3686
  • [28] Recent Progress in Hydrogen Bond-Mediated Transformations to Chiral Medicinal Drugs by Phosphoric Acid and Thiourea Derived Organocatalysts
    Bhadury, Pinaki S.
    Pang, Jun
    [J]. CURRENT ORGANIC CHEMISTRY, 2022, 26 (01) : 2 - 5
  • [30] Engineered Immobilised Organocatalysts for the Synthesis of Chiral Amines
    Macia, Maria
    Munoz, Ivan
    Porcar, Raul
    Cirujano, Francisco G.
    Altava, Belen
    Luis, Santiago V.
    Garcia-Verdugo, Eduardo
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (04) : 892 - 899