Asymmetric synthesis of α-amino acids using polymer-supported Cinchona alkaloid-derived ammonium salts as chiral phase-transfer catalysts

被引:98
|
作者
Chinchilla, R [1 ]
Mazón, P [1 ]
Nájera, C [1 ]
机构
[1] Univ Alicante, Dept Quim Organ, E-03080 Alicante, Spain
关键词
D O I
10.1016/S0957-4166(00)00317-7
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Cinchonidine and cinchonine have been N-alkylated with Merrifield resin and employed as chiral phase-transfer catalysts for the enantioselective alkylation of enolates from N-(diphenylmethylene)glycine esters with activated electrophiles (up to 90% ee). The use of the polymer-supported cinchonidine ammonium salt afforded the corresponding (S)-isomers, whereas the (R)-isomers were obtained using related cinchonine-supported polymers. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3277 / 3281
页数:5
相关论文
共 50 条
  • [41] MECHANISM OF REACTIONS PROMOTED BY POLYMER-SUPPORTED PHASE-TRANSFER CATALYSTS
    MONTANARI, F
    QUICI, S
    TUNDO, P
    JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (02): : 199 - 202
  • [42] POLYMER-SUPPORTED MULTI-SITE PHASE-TRANSFER CATALYSTS
    IDOUX, JP
    WYSOCKI, R
    YOUNG, S
    TURCOT, J
    OHLMAN, C
    LEONARD, R
    SYNTHETIC COMMUNICATIONS, 1983, 13 (02) : 139 - 144
  • [43] REACTIVITY AND APPLICATIONS OF SOLUBLE AND POLYMER-SUPPORTED PHASE-TRANSFER CATALYSTS
    MONTANARI, F
    LANDINI, D
    MAIA, AM
    QUICI, S
    ANELLI, PL
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1985, 190 (SEP): : 11 - PER
  • [44] REACTIVITY AND APPLICATION OF SOLUBLE AND POLYMER-SUPPORTED PHASE-TRANSFER CATALYSTS
    MONTANARI, F
    LANDINI, D
    MAIA, A
    QUICI, S
    ANELLI, PL
    ACS SYMPOSIUM SERIES, 1987, 326 : 54 - 66
  • [45] POLYMER-SUPPORTED OPTICALLY-ACTIVE PHASE-TRANSFER CATALYSTS
    SHERRINGTON, DC
    KELLY, J
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1982, 183 (MAR): : 108 - POLY
  • [46] POLYMER-SUPPORTED PHASE-TRANSFER CATALYSTS - REACTION-MECHANISMS
    FORD, WT
    TOMOI, M
    ADVANCES IN POLYMER SCIENCE, 1984, 55 : 49 - 104
  • [47] POLYMER-SUPPORTED PHOSPHORIC TRIAMIDES AS CATALYSTS FOR PHASE-TRANSFER REACTIONS
    TOMOI, M
    IKEDA, M
    KAKIUCHI, H
    TETRAHEDRON LETTERS, 1978, (39) : 3757 - 3758
  • [48] Chiral cinchona alkaloid-derived thiourea catalyst for enantioselective synthesis of novel ß-amino esters by mannich reaction
    Li, Weihua
    Song, Baoan
    Bhadury, Pinaki S.
    Li, Liang
    Wang, Zhenchao
    Zhang, Xiaoyan
    Hu, Deyu
    Chen, Zhuo
    Zhang, Yuping
    Bai, Song
    Wu, Jian
    Yang, Song
    CHIRALITY, 2012, 24 (03) : 223 - 231
  • [49] Powerful chiral phase-transfer catalysts for the asymmetric synthesis of α-alkyl- and α,α,-dialkyl-α-amino acids
    Kitamra, M
    Shirakawa, S
    Maruoka, K
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (10) : 1549 - 1551
  • [50] POLYMER-SUPPORTED PHASE-TRANSFER CATALYSTS - HIGH CATALYTIC ACTIVITY OF AMMONIUM AND PHOSPHONIUM QUATERNARY-SALTS BONDED TO A POLYSTYRENE MATRIX
    MOLINARI, H
    MONTANARI, F
    QUICI, S
    TUNDO, P
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (14) : 3920 - 3927