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
  • [41] Origins of Selectivity and General Model for Chiral Phosphoric Acid-Catalyzed Oxetane Desymmetrizations
    Champagne, Pier Alexandre
    Houk, K. N.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (38) : 12356 - 12359
  • [42] Chiral BINOL-derived phosphoric acids: privileged Bronsted acid organocatalysts for C-C bond formation reactions
    Zamfir, Alexandru
    Schenker, Sebastian
    Freund, Matthias
    Tsogoeva, Svetlana B.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (23) : 5262 - 5276
  • [43] Stereoselective Reactions Promoted by Alkali Metal Salts of Phosphoric Acid Organocatalysts
    Cocco, Emanuele
    Antenucci, Achille
    Carlone, Armando
    Manini, Paola
    Pesciaioli, Fabio
    Dughera, Stefano
    [J]. CHEMCATCHEM, 2024,
  • [44] A versatile synthesis of chiral β-aminophosphines
    Su, Hsin Y.
    Song, Yixiong
    Taylor, Mark S.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (24) : 5665 - 5672
  • [45] Recyclable fluorous cinchona organocatalysts for asymmetric synthesis of biologically interesting compounds
    Huang, Xin
    Zhang, Wei
    [J]. CHEMICAL COMMUNICATIONS, 2021, 57 (79) : 10116 - 10124
  • [46] Alkaloid synthesis using chiral secondary amine organocatalysts
    Ishikawa, Hayato
    Shiomi, Shinya
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (02) : 409 - 424
  • [47] Design, synthesis, and evaluation of chiral thiophosphorus acids as organocatalysts
    Winters, Karen R.
    Montchamp, Jean-Luc
    [J]. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2022, 18 : 1471 - 1478
  • [48] Synthesis of Chiral Phosphorous and Phosphoric Acid Derivatives from the Lignans Matairesinol and Conidendrin
    Brusentsev, Yury
    Eklund, Patrik
    [J]. SYNLETT, 2016, 27 (18) : 2557 - 2560
  • [49] Endo-Functionalized Cyclic Oligophenylenes: Synthesis and Complexation with a Chiral Phosphoric Acid
    Ono, Kosuke
    Tanaka, Yusei
    Sugimoto, Kana
    Kinubari, Shigemi
    Kawai, Hidetoshi
    [J]. ACS OMEGA, 2022, : 45347 - 45352
  • [50] Asymmetric Synthesis of Griffipavixanthone Employing a Chiral Phosphoric Acid-Catalyzed Cycloaddition
    Smith, Michael J.
    Reichl, Kyle D.
    Escobar, Randolph A.
    Heavey, Thomas J.
    Coker, David F.
    Schaus, Scott E.
    Porco, John A., Jr.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (01) : 148 - 153