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
来源：
TETRAHEDRON-ASYMMETRY | 2000年 / 11卷 / 16期
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
  • [21] Calixarene-based chiral phase-transfer catalysts derived from cinchona alkaloids for enantioselective synthesis of α-amino acids
    Bozkurt, Selahattin
    Durmaz, Mustafa
    Yilmaz, Mustafa
    Sirit, Abdulkadir
    TETRAHEDRON-ASYMMETRY, 2008, 19 (05) : 618 - 623
  • [22] Highly enantioselective and practical cinchona-derived phase-transfer catalysts for the synthesis of α-amino acids
    Park, HG
    Jeong, BS
    Yoo, MS
    Lee, JH
    Park, MK
    Lee, YJ
    Kim, MJ
    Jew, SS
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2002, 41 (16) : 3036 - 3038
  • [23] Dimeric cinchona ammonium salts with benzophenone linkers: enantioselective phase transfer catalysts for the synthesis of α-amino acids
    Woo, Seunga
    Kim, Yong-Gyun
    Lim, Baegeun
    Oh, Jiin
    Lee, Yeonji
    Gwon, Hyeri
    Nahm, Keepyung
    RSC ADVANCES, 2018, 8 (04): : 2157 - 2160
  • [24] THE ASYMMETRIC SYNTHESIS OF AMINO ACIDS UNDER POLYMER-SUPPORTED PHASE TRANSFER CATALYTIC CONDITION
    王咏梅
    张政朴
    王真
    孟继本
    霍奇
    Chinese Journal of Polymer Science, 1998, (04) : 356 - 361
  • [25] The asymmetric synthesis of amino acids under polymer-supported phase transfer catalytic condition
    Wang, YM
    Zhang, ZP
    Wang, Z
    Meng, JB
    Hodge, P
    CHINESE JOURNAL OF POLYMER SCIENCE, 1998, 16 (04) : 356 - 361
  • [26] Synthesis of dialkyl peroxides in the presence of polymer-supported phase-transfer catalysts
    Baj, Stefan
    Siewniak, Agnieszka
    Socha, Beata
    APPLIED CATALYSIS A-GENERAL, 2006, 309 (01) : 85 - 90
  • [27] Cinchona Alkaloid-derived Polymer Catalysts for Asymmetric Aza-Michael Addition of Aniline to Chalcone
    Rahman, Mohammad F.
    Fujisawa, Ikuhide
    Haraguchi, Naoki
    Itsuno, Shinichi
    CHEMISTRY LETTERS, 2023, 52 (06) : 422 - 425
  • [28] Novel polymer-supported chiral catalysts for asymmetric synthesis
    Itsuno, S
    Kamahori, K
    Watanabe, K
    Ito, K
    MACROMOLECULAR SYMPOSIA, 1996, 105 : 155 - 159
  • [29] POLYMER-SUPPORTED CHIRAL CATALYSTS IN ASYMMETRIC SYNTHESIS.
    Stille, J.K.
    1689, (A21): : 13 - 14
  • [30] POLYMER-SUPPORTED CRYPTANDS AS CATALYSTS FOR PHASE-TRANSFER REACTIONS
    TOMOI, M
    KIHARA, K
    KAKIUCHI, H
    TETRAHEDRON LETTERS, 1979, 20 (36) : 3485 - 3486
12345