Polystyrene-bound cinchona alkaloids: Application to enantioselective electrophilic fluorination of silyl enol ethers

被引:18
|
作者
Thierry, B [1 ]
Audouard, C [1 ]
Plaquevent, JC [1 ]
Cahard, D [1 ]
机构
[1] Univ Rouen, IRCOF, CNRS, UMR 6014, F-76821 Mont St Aignan, France
关键词
polymer; cinchona alkaloids; enantioselective synthesis; electrophilic fluorination;
D O I
10.1055/s-2004-817781
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A panoply of new polystyrene-bound cinchona alkaloids (PS-CA) has been prepared, and exploited for the design of unprecedented enantioselective electrophilic fluorinating agents. Compared to nonsupported [N-F](+) reagents, the polystyrene-bound N-fluoro ammonium salts of cinchona alkaloids show comparable efficiency and ready purification of the fluorinated reaction products. One PS-CA was recycled 3 times without loss of stereochemical performance.
引用
收藏
页码:856 / 860
页数:5
相关论文
共 50 条
  • [1] Cinchona alkaloid catalyzed enantioselective fluorination of allyl silanes, silyl enol ethers, and oxindoles
    Ishimaru, Takehisa
    Shibata, Norio
    Horikawa, Takao
    Yasuda, Naomi
    Nakamura, Shuichi
    Toru, Takeshi
    Shiro, Motoo
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (22) : 4157 - 4161
  • [2] N-Fluoro Ammonium salts of Cinchona Alkaloids in Enantioselective Electrophilic Fluorination
    Shibata, Norio
    Cahard, Dominique
    CHEMICAL RECORD, 2023, 23 (09):
  • [3] Electrophilic heterocycles: Functionalization with enol silyl ethers
    Holmin, Grant P.
    Hood, Jacob C.
    Xue, Hongfang
    Klumpp, Douglas A.
    TETRAHEDRON, 2023, 142
  • [4] Electrophilic fluorination mediated by cinchona alkaloids:: Highly enantioselective synthesis of α-fluoro-α-phenylglycine derivatives
    Mohar, B
    Baudoux, M
    Plaquevent, JC
    Cahard, D
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2001, 40 (22) : 4214 - 4216
  • [5] Catalytic enantioselective amination of silyl enol ethers.
    Evans, DA
    Johnson, DS
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1998, 216 : U514 - U514
  • [6] Highly enantioselective epoxidation of enol silyl ethers and esters
    Zhu, YM
    Tu, Y
    Yu, HW
    Shi, Y
    TETRAHEDRON LETTERS, 1998, 39 (43) : 7819 - 7822
  • [7] Enantioselective Rh-Catalyzed Hydroboration of Silyl Enol Ethers
    Dong, Wenke
    Xu, Xin
    Ma, Honghui
    Lei, Yaqin
    Lin, Zhenyang
    Zhao, Wanxiang
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (29) : 10902 - 10909
  • [8] Enantioselective electrophilic fluorination: a study of the fluorine-transfer from achiral N-F reagents to cinchona alkaloids
    Baudequin, C
    Loubassou, JF
    Plaquevent, JC
    Cahard, D
    JOURNAL OF FLUORINE CHEMISTRY, 2003, 122 (02) : 189 - 193
  • [9] Enantioselective Bromination of Silyl Enol Ethers with Chiral Pentacarboxycyclopentadienyl Bromide
    Liu, Guo
    Li, Pingfan
    SYNLETT, 2023, 34 (20) : 2447 - 2450
  • [10] Enantioselective copper-catalyzed cyclopropanation of silyl enol ethers
    Ebinger, A
    Heinz, T
    Umbricht, G
    Pfaltz, A
    TETRAHEDRON, 1998, 54 (35) : 10469 - 10480