Chiral Dawson-Type Hybrid Polyoxometalate Catalyzes Enantioselective Diels-Alder Reactions

被引：19
|
作者：
Xuan, Wen-Jing [1 ,2 ]
Botuha, Candice [1 ,2 ]
Hasenknopf, Bernold [1 ,2 ]
Thorimbert, Serge [1 ,2 ]
机构：
[1] Sorbonne Univ, Univ Paris 06, UMR 8232, Inst Parisien Chim Mol, F-75005 Paris, France
[2] CNRS, UMR 8232, IPCM, F-75005 Paris, France
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2015年 / 21卷 / 46期
关键词：
chirality; cycloaddition; Diels-Alder reaction; organocatalysis; polyoxometalates; HIGHLY EFFICIENT; HETEROGENEOUS CATALYSIS; SPONTANEOUS RESOLUTION; ASYMMETRIC CATALYSIS; BUILDING-BLOCKS; AMINO-ACIDS; METAL-OXIDE; CLUSTERS; DESIGN; ORGANOCATALYSTS;
D O I：
10.1002/chem.201502839
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Can achiral organocatalysts linked to chiral polyanionic metal oxide clusters provide good selectivity in enantioselective CC bond formations? The answer to this question is investigated by developing a new active hybrid polyoxometalate-based catalyst for asymmetric Diels-Alder reaction. Chirality transfer from the chiral anionic polyoxometalate to the covalently linked achiral imidazolidinone allows Diels-Alder cycloaddition products to be obtained with good yields and high enantioselectivities when using cyclopentadiene and acrylaldehydes as partners.
引用
收藏
页码：16512 / 16516
页数：5
相关论文
共 50 条
  • [1] Enantioselective Organocatalytic Diels-Alder Reactions
    Merino, Pedro
    Marques-Lopez, Eugenia
    Tejero, Tomas
    Herrera, Raquel P.
    SYNTHESIS-STUTTGART, 2010, (01): : 1 - 26
  • [2] How Ionization Catalyzes Diels-Alder Reactions
    Vermeeren, Pascal
    Hamlin, Trevor A.
    Bickelhaupt, F. Matthias
    CHEMISTRY-A EUROPEAN JOURNAL, 2022, 28 (40) : e202201620
  • [3] Highly Enantioselective Diels-Alder Reaction Catalyzed by Chiral Imidazolidinone
    Wang, Yongjiang
    Xu, Xiaoliang
    Pei, Wen
    SYNTHETIC COMMUNICATIONS, 2009, 39 (11) : 2032 - 2041
  • [4] Expanding the Chiral Monoterpene Pool: Enantioselective Diels-Alder Reactions of α-Acyloxy Enones
    Mendoza, Skyler D.
    Rombola, Michael
    Tao, Yujia
    Zuend, Stephan J.
    Goetz, Roland
    McLaughlin, Martin J.
    Reisman, Sarah E.
    ORGANIC LETTERS, 2022, 24 (21) : 3802 - 3806
  • [5] Enantioselective Redox-Divergent Chiral Phosphoric Acid Catalyzed Quinone Diels-Alder Reactions
    Varlet, Thomas
    Gelis, Coralie
    Retailleau, Pascal
    Bernadat, Guillaume
    Neuville, Luc
    Masson, Geraldine
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (22) : 8491 - 8496
  • [6] Enantioselective Diels-Alder Reactions with Anomalous endo/exo Selectivities Using Conformationally Flexible Chiral Supramolecular Catalysts
    Hatano, Manabu
    Mizuno, Tomokazu
    Izumiseki, Atsuto
    Usami, Ryota
    Asai, Takafumi
    Akakura, Matsujiro
    Ishihara, Kazuaki
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (51) : 12189 - 12192
  • [7] A novel hydrazide type organocatalyst for enantioselective Diels-Alder reactions
    Suzuki, Ichiro
    Ando, Masafumi
    Shimabara, Rumiko
    Hirata, Ai
    Takeda, Kei
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (08) : 3033 - 3040
  • [8] Highly enantioselective access to cannabinoid-type tricyles by organocatalytic Diels-Alder reactions
    Braese, Stefan
    Volz, Nicole
    Glaeser, Franziska
    Nieger, Martin
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2012, 8 : 1385 - 1392
  • [9] Catalytic and Enantioselective Diels-Alder Reaction of Siloxydienes
    Harada, Shinji
    Nishida, Atsushi
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 8 (06) : 732 - 745
  • [10] Highly enantioselective Diels-Alder catalysis with a chiral ruthenium bisoxazoline complex
    Faller, JW
    Lavoie, A
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 630 (01) : 17 - 22
12345