Dimeric cinchona ammonium salts with benzophenone linkers: enantioselective phase transfer catalysts for the synthesis of α-amino acids

被引:9
|
作者
Woo, Seunga [1 ]
Kim, Yong-Gyun [1 ]
Lim, Baegeun [1 ]
Oh, Jiin [1 ]
Lee, Yeonji [1 ]
Gwon, Hyeri [1 ]
Nahm, Keepyung [1 ]
机构
[1] Yeungnam Univ, Sch Chem & Biochem, 280 Daehak Ro, Gyongsan 38541, Gyeongbuk, South Korea
来源
RSC ADVANCES | 2018年 / 8卷 / 04期
基金
新加坡国家研究基金会;
关键词
ASYMMETRIC CATALYSIS; CHIRAL POLYMERS; SCHIFF-BASE; ALKYLATION; ALKALOIDS; ENOLATE; IMINES; STATE;
D O I
10.1039/c7ra12499f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Chiral phase transfer catalysts of dimeric cinchona ammonium salts linked with a benzophenone bridge showed high enantioselectivity in the alpha-alkylation of a glycinate ester under mild industry-applicable conditions: 0.5 mol% PTC and near equivalents of alkyl halide. A dual function of the dimeric quinuclidiniums was proposed for the high efficiency.
引用
收藏
页码:2157 / 2160
页数:4
相关论文
共 50 条
  • [31] Thiourea-phosphonium salts from amino acids: cooperative phase-transfer catalysts in the enantioselective aza-Henry reaction
    Cao, Dongdong
    Chai, Zhuo
    Zhang, Jiaxing
    Ye, Zhengqing
    Xiao, Hua
    Wang, Hongyu
    Chen, Jinhao
    Wu, Xiaoyu
    Zhao, Gang
    CHEMICAL COMMUNICATIONS, 2013, 49 (53) : 5972 - 5974
  • [32] Cinchona alkaloid-based polymer-bound phase-transfer catalysts: Efficient enantioselective alkylation of benzophenone imine of glycine esters
    Thierry, Baptiste
    Plaquevent, Jean-Christophe
    Cahard, Dominique
    MOLECULAR DIVERSITY, 2005, 9 (04) : 277 - 290
  • [33] Cinchona alkaloid-based polymer-bound phase-transfer catalysts: Efficient enantioselective alkylation of benzophenone imine of glycine esters
    Baptiste Thierry
    Jean-Christophe Plaquevent
    Dominique Cahard
    Molecular Diversity, 2005, 9 : 277 - 290
  • [34] Synthesis and catalytic activities of bicyclic chiral ammonium salt phase-transfer catalysts based on natural amino acids
    Shen, ZX
    Kong, AD
    Shi, M
    Zhang, YW
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2003, 23 (07) : 701 - 704
  • [35] Novel quaternary ammonium salts as phase-transfer catalysts
    Hollingsworth, Brian E.
    West, Christy Wheeler
    O'Brien, Richard A.
    Davis, James H.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
  • [36] Enantioselective synthesis of fluorinated aromatic amino acids catalyzed by SPINOL-derived chiral quaternary ammonium salts
    Rong, Meng-Yu
    Nie, Jing
    Li, Shen
    Ma, Jun-An
    MOLECULAR CATALYSIS, 2024, 552
  • [37] Ultrasonic assisted dimeric cinchona based chiral phase transfer catalysts for highly enanatioselective synthesis of epoxidation of α,β-unsaturated ketones
    Sivamani, Jayaraman
    Ashokkumar, Veeramanoharan
    Sadhasivam, Velu
    Duraimurugan, Kumaraguru
    Siva, Ayyanar
    RSC ADVANCES, 2014, 4 (104): : 60293 - 60299
  • [38] Asymmetric synthesis of β- amino ketones by using cinchona alkaloid- based chiral phase transfer catalysts
    Li, Weihua
    Wang, Yifeng
    Xu, Danqian
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (45) : 8704 - 8709
  • [39] Enantioselective quaternization of 4-substituted oxazol-5-(4H)-ones using recoverable Cinchona-derived dimeric ammonium salts as phase-transfer organocatalysts
    Tari, Silvia
    Avila, Angel
    Chinchilla, Rafael
    Najera, Carmen
    TETRAHEDRON-ASYMMETRY, 2012, 23 (02) : 176 - 180
  • [40] A new trimeric cinchona alkaloid as a chiral phase-transfer catalyst for the synthesis of asymmetric α-amino acids
    Siva, A
    Murugan, E
    SYNTHESIS-STUTTGART, 2005, (17): : 2927 - 2933