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
  • [31] Synthesis and Characterization of Ethylene Glycol Substituted Poly(phenylene Vinylene) Derivatives
    Wang, Chun-Chih
    Tsai, Hsinhan
    Shih, Hung-Hsin
    Jeon, Seaho
    Xu, Zhihua
    Williams, Darrick
    Iyer, Srinivas
    Sanchez, Timothy C.
    Wang, Leeyih
    Cotlet, Mircea
    Wang, Hsing-Lin
    ACS APPLIED MATERIALS & INTERFACES, 2010, 2 (03) : 738 - 747
  • [32] A facile synthesis of branched poly(ethylene glycol) and its heterobifunctional derivatives
    Li, Zhongyu
    Chau, Ying
    POLYMER CHEMISTRY, 2011, 2 (04) : 873 - 878
  • [33] Combinatorial synthesis of novel thiourea derivatives on a modified poly(ethylene glycol)
    Yang, GC
    Chen, ZX
    Zhang, ZJ
    REACTIVE & FUNCTIONAL POLYMERS, 2002, 51 (01): : 1 - 6
  • [34] Enantioselective synthesis of α,β-diamino ester derivatives: memory of chirality in imino-aldol reactions
    Ghorai, Manas K.
    Ghosh, Koena
    Yadav, A. K.
    TETRAHEDRON LETTERS, 2009, 50 (04) : 476 - 479
  • [35] Poly(ethylene glycol)-supported tetrahydroxyphenyl porphyrin: A convenient, recyclable catalyst for photooxidation reactions
    Benaglia, M
    Danelli, T
    Fabris, F
    Sperandio, D
    Pozzi, G
    ORGANIC LETTERS, 2002, 4 (24) : 4229 - 4232
  • [36] Soluble-polymer-supported synthesis of β-lactams on a modified poly(ethylene glycol)
    Annunziata, R
    Benaglia, M
    Cinquini, M
    Cozzi, F
    CHEMISTRY-A EUROPEAN JOURNAL, 2000, 6 (01) : 133 - 138
  • [37] Application of bifunctional poly(ethylene glycol) derivatives in the activation of cellulose supports.
    Pope, JD
    Dressel, RM
    Lane, JW
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1999, 217 : U128 - U128
  • [38] Application of star poly(ethylene glycol) derivatives in drug delivery and controlled release
    Zhao, Xiaobao
    Si, Jingxing
    Huang, Dongsheng
    Li, Ke
    Xin, Ying
    Sui, Meihua
    JOURNAL OF CONTROLLED RELEASE, 2020, 323 : 565 - 577
  • [39] Poly(ethylene glycol) supported chiral quaternary ammonium salts as phase-transfer catalysts for catalytic enantioselective synthesis of α-amino acids
    Kim, DY
    Huh, SC
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2004, 25 (03): : 347 - 348
  • [40] Synthesis and Characterization of Calix[4]arene Functionalized Poly(ethylene glycol) Derivatives
    Jinyu Shen
    H. Fred Koch
    D. Max Roundhill
    Journal of inclusion phenomena and macrocyclic chemistry, 2000, 38 : 57 - 67
12345