Synthesis of Poly(Ethylene Glycol)-Supported (R)-BINOL Derivatives and Their First Application in Enantioselective Mukaiyama Aldol Reactions

被引：8
作者：
Zimmer, Reinhold [1 ]
Dekaris, Vjekoslav [1 ]
Knauer, Markus [1 ]
Schefzig, Luise [1 ]
Reissig, Hans-Ulrich [1 ]
机构：
[1] Free Univ Berlin, Inst Chem & Biochem, D-14195 Berlin, Germany
来源：
SYNTHETIC COMMUNICATIONS | 2009年 / 39卷 / 06期
关键词：
Aldol reaction; asymmetric catalysis; binaphthalene; chiral additives; poly(ethylene glycol); polymer-supported reaction; thioester; CATALYTIC ASYMMETRIC ALLYLATION; CARBONYL-ENE; TITANIUM CATALYST; LEWIS-ACID; BINOL; LIGANDS; DIETHYLZINC; COMPLEXES; ALDEHYDES; MICHAEL;
D O I：
10.1080/00397910802455080
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The Mukaiyama aldol reaction of 2-styryl-oxazole-4-carbaldehyde (1) as model substrate with S-ketene silyl acetal 2 catalyzed by poly(ethylene glycol)-supported binaphthyl-derived chiral titanium(IV) complexes afforded the corresponding aldol product in good to excellent yields and enantioselectivities up to 94% ee. The chemical yields and/or the enantioselectivities are enhanced by generating the active catalyst from Ti(OiPr)4, polymer-supported ligands (R)-6 or (R)-8, and chiral or achiral promoters. Pyrrolidine derivative (S)-13 and trifluoromethyl-substituted phenol 12 are the most efficient additives found.
引用
收藏
页码：1012 / 1026
页数：15
相关论文
共 50 条
  • [41] Synthesis of polymer networks by means of addition reactions of tri-amine and poly(ethylene glycol) diacrylate or diglycidyl ether compounds
    Naofumi Naga
    Daisuke Inose
    Tomomi Ishida
    Kyohei Kubota
    Hassan Nageh
    Tamaki Nakano
    Polymer Bulletin, 2021, 78 : 2745 - 2763
  • [42] Novel magnetic iron oxide nanoparticles coated with poly(ethylene imine)-g-poly(ethylene glycol) for potential biomedical application: Synthesis, stability, cytotoxicity and MR imaging
    Schweiger, Christoph
    Pietzonka, Clemens
    Heverhagen, Johannes
    Kissel, Thomas
    INTERNATIONAL JOURNAL OF PHARMACEUTICS, 2011, 408 (1-2) : 130 - 137
  • [43] Synthesis of a novel poly(ethylene glycol) grafted triethylamine functionalized dicationic ionic liquid and its application in one-pot synthesis of 2-amino-2-chromene derivatives in water
    Wang, Yinglei
    Yue, Chun
    Li, Xia
    Luo, Jun
    COMPTES RENDUS CHIMIE, 2016, 19 (08) : 1021 - 1026
  • [44] Efficient synthesis of zirconium poly(styrene-phenylvinylphosphonate)phosphate-supported proline as a recyclable catalyst for direct asymmetric aldol reactions in water
    Wu, Chuanlong
    Long, Xiaoqin
    Fu, Xiangkai
    Wang, Guangwei
    Mirza, Zakaria A.
    RSC ADVANCES, 2015, 5 (05): : 3168 - 3176
  • [45] Novel poly(ethylene glycol) derivatives with carboxylic acid pendant groups: synthesis and their protection and enhancing effect on non-viral gene transfection systems
    Koyama, Y
    Ito, T
    Matsumoto, H
    Tanioka, A
    Okuda, T
    Yamaura, N
    Aoyagi, H
    Niidome, T
    JOURNAL OF BIOMATERIALS SCIENCE-POLYMER EDITION, 2003, 14 (06) : 515 - 531
  • [46] Synthesis of a novel 8-hydroxyquinoline functionalized poly (ethylene glycol) bridged dicationic ionic liquid and its application in palladium-catalyzed Heck reaction under solvent-free conditions
    Wang, Yinglei
    Luo, Jun
    Liu, Zuliang
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2013, 739 : 1 - 5
  • [47] Synthesis of a Novel Diol-Functionalized Poly(ethylene glycol)-Bridged Dicationic Ionic Liquid and its Application in Copper-Catalyzed Amination of Aryl Halides
    Wang, Yinglei
    Luo, Jun
    Hou, Tianjiao
    Liu, Zuliang
    AUSTRALIAN JOURNAL OF CHEMISTRY, 2013, 66 (05) : 586 - 593
  • [48] Synthesis of a novel poly (ethylene glycol) grafted N,N-dimethylaminopyridine functionalized dicationic ionic liquid and its application in one-pot synthesis of 3,4-dihydropyrano[3,2-c]chromene derivatives in water
    Wang, Yinglei
    Ye, Hongyong
    Zuo, Guangling
    Luo, Jun
    JOURNAL OF MOLECULAR LIQUIDS, 2015, 212 : 418 - 422
  • [49] RETRACTED: An Efficient Synthesis of Poly(ethylene glycol)-Supported Iron(II) Porphyrin using a Click Reaction and its Application for the Catalytic Olefination of Aldehydes (Retracted article. See vol. 353, pg. 1391, 2011)
    Jain, Suman L.
    Joseph, Jomy K.
    Kuehn, Fritz E.
    Reiser, Oliver
    ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (1-2) : 230 - 234
  • [50] Synthesis of new fluorous modular chiral ligand derivatives from amino alcohols and application in enantioselective carbon-carbon bond-forming alkylation reactions
    Sehnem, Jasquer A.
    Milani, Priscila
    Nascimento, Vanessa
    Andrade, Leandro H.
    Dorneles, Luciano
    Braga, Antonio L.
    TETRAHEDRON-ASYMMETRY, 2010, 21 (08) : 997 - 1003
12345