Poly[(S)-3-acrylamide-2,2'-dihydroxy-1,1'-binaphthyl]: Synthesis and Application in the Asymmetric Addition of Diethylzinc to Aromatic Aldehydes

被引:1
|
作者
Zhang, Xun [1 ]
Yang, Nianfa [1 ]
机构
[1] Xiangtan Univ, Key Lab Environm Friendly Chem & Applicat, Minist Educ, Coll Chem, Xiangtan 411105, Peoples R China
关键词
polyacrylamide; 1,1'-bi-2-naphthol; Et2Zn; aromatic aldehydes; asymmetric addition; CATALYTIC ENANTIOSELECTIVE ADDITION; CHIRAL LIGANDS; BINOL; BASE;
D O I
10.6023/cjoc201611027
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Poly[(S)-3-acrylamide-2,2'-dihydroxy-1,1'-binaphthyl](poly-6) was synthesized through radical polymerization and applied in the asymmetric addition of diethylzinc to aromatic aldehydes, giving the optically active products up to 95% enantiomeric excess (ee). Besides, The poly-6 could be recycled up to six times without erosion of the enantioselectivity.
引用
收藏
页码:1027 / 1032
页数:6
相关论文
共 29 条
  • [1] Enantioselective Mannich-type reaction catalyzed by a chiral Bronsted acid
    Akiyama, T
    Itoh, J
    Yokota, K
    Fuchibe, K
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (12) : 1566 - 1568
  • [2] Immobilization of heterobimetallic multifunctional asymmetric catalyst
    Arai, T
    Hu, QS
    Zheng, XF
    Pu, L
    Sasai, H
    [J]. ORGANIC LETTERS, 2000, 2 (26) : 4261 - 4263
  • [3] Modified BINOL ligands in asymmetric catalysis
    Chen, Y
    Yekta, S
    Yudin, AK
    [J]. CHEMICAL REVIEWS, 2003, 103 (08) : 3155 - 3211
  • [4] Atroposelective Synthesis of Axially Chiral Biaryldiols via Organocatalytic Arylation of 2-Naphthols
    Chen, Ye-Hui
    Cheng, Dao-Juan
    Zhang, Jian
    Wang, Yong
    Liu, Xin-Yuan
    Tan, Bin
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (48) : 15062 - 15065
  • [5] Optically Active Helical Poly[(S)-3-vinyl-2,2′-dihydroxy-1,1′-binaphthyl]: New Ligand for Asymmetric Addition of Diethylzinc to Aryl Aldehyde
    Chen, Yehui
    Qin, Guochang
    Yang, Liwen
    Yang, Nianfa
    [J]. CHINESE JOURNAL OF CHEMISTRY, 2015, 33 (04) : 463 - 466
  • [6] Enantioselective addition of diethylzinc to aromatic aldehydes catalyzed by Ti(IV) complexes of C2-symmetrical chiral BINOL derivatives
    Gou, Shaohua
    Judeh, Zaher M. A.
    [J]. TETRAHEDRON LETTERS, 2009, 50 (03) : 281 - 283
  • [7] Enantioselective alkylation of aldehydes catalyzed by a highly active titanium complex of 3-substituted unsymmetric BINOL
    Harada, Toshiro
    Kanda, Kousou
    [J]. ORGANIC LETTERS, 2006, 8 (17) : 3817 - 3819
  • [8] Structurally rigid and optically active dendrimers
    Hu, QS
    Pugh, V
    Sabat, M
    Pu, L
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (20): : 7528 - 7536
  • [9] Asymmetric catalysis of the Friedel-Crafts reaction with fluoral by chiral binaphthol-derived titanium catalysts through asymmetric activation
    Ishii, A
    Soloshonok, VA
    Mikami, K
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (05): : 1597 - 1599
  • [10] Dendrimers containing chiral ferrocenyl diphosphine ligands for asymmetric catalysis
    Köllner, C
    Pugin, B
    Togni, A
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (39) : 10274 - 10275