A novel quaternary ammonium salts derived from α-amino acids with large steric hindrance group and its application in asymmetric Mannich reaction

被引：4
作者：
Tian, Zhengtao [1 ]
Meng, Xiangyu [2 ]
Luo, Yueyang [2 ]
Cao, Shaokui [1 ]
Zhao, Gang [2 ]
机构：
[1] Zhengzhou Univ, Sch Mat Sci & Engn, Zhengzhou 450001, Peoples R China
[2] Chinese Acad Sci, Ctr Excellence Mol Synth, Shanghai Inst Organ Chem, Key Lab Synthet Chem Nat Subst, 345 Lingling Rd, Shanghai 200032, Peoples R China
来源：
TETRAHEDRON | 2020年 / 76卷 / 39期
基金：
中国国家自然科学基金;
关键词：
Quaternary ammonium salt; Amino acid; Large steric hindrance group; Mannich reaction; PHASE-TRANSFER CATALYSTS; ENANTIOSELECTIVE SYNTHESIS; IMINO ESTERS; CYCLOADDITION; DERIVATIVES; KETOESTERS; TARTRATE; DESIGN;
D O I：
10.1016/j.tet.2020.131484
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Quaternary ammonium salts derived from amino acids with large steric hindrance group have been designed and synthesized, which promoted the asymmetric Mannich reaction of glycine imines with N-Boc-aldimines in excellent yields with high enantio- and diastereo-control compared with known catalysts of this type reported by our group. (C) 2020 Elsevier Ltd. All rights reserved.
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页数：12
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共 49 条
  • [1] Cyclopropenimine-Catalyzed Enantioselective Mannich Reactions of tert-Butyl Glycinates with N-Boc-Imines
    Bandar, Jeffrey S.
    Lambert, Tristan H.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (32) : 11799 - 11802
  • [2] Organocatalytic Asymmetric Cyanosilylation of Nitroalkenes
    Bernal, Pablo
    Fernandez, Rosario
    Lassaletta, Jose M.
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (26) : 7714 - 7718
  • [3] Asymmetric Ion-Pairing Catalysis
    Brak, Katrien
    Jacobsen, Eric N.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (02) : 534 - 561
  • [4] 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
    [J]. CHEMICAL COMMUNICATIONS, 2013, 49 (53) : 5972 - 5974
  • [5] Efficient organocatalysts derived from simple chiral acyclic amino acids in asymmetric catalysis
    Chai, Zhuo
    Zhao, Gang
    [J]. CATALYSIS SCIENCE & TECHNOLOGY, 2012, 2 (01) : 29 - 41
  • [6] Bicyclic guanidinium-catalyzed enantioselective phase-transfer alkylation: direct access to pyrroloindolines and furoindolines
    Chen, Wenchao
    Yang, Wenguo
    Yan, Lin
    Tan, Choon-Hong
    Jiang, Zhiyong
    [J]. CHEMICAL COMMUNICATIONS, 2013, 49 (84) : 9854 - 9856
  • [7] EFFICIENT CATALYTIC ASYMMETRIC ALKYLATIONS .1. ENANTIOSELECTIVE SYNTHESIS OF (+)-INDACRINONE VIA CHIRAL PHASE-TRANSFER CATALYSIS
    DOLLING, UH
    DAVIS, P
    GRABOWSKI, EJJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (02) : 446 - 447
  • [8] Highly enantioselective 1,3-dipolar cycloaddition of imino esters with benzofuranone derivatives catalyzed by thiourea-quaternary ammonium salt
    Du, Ting
    Li, Zhaokun
    Zheng, Changwu
    Fang, Guosheng
    Yu, Longhui
    Liu, Jun
    Zhao, Gang
    [J]. TETRAHEDRON, 2018, 74 (52) : 7485 - 7494
  • [9] Enantioselective Synthesis of Dialkylated α-Hydroxy Carboxylic Acids through Asymmetric Phase-Transfer Catalysis
    Duan, Shaobo
    Li, Sanliang
    Ye, Xinyi
    Du, Nuan-Nuan
    Tan, Choon-Hong
    Jiang, Zhiyong
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (15) : 7770 - 7778
  • [10] Research Progress in Key Technologies on Near Infrared Microspectrometer
    Fan, Yu
    Quan, Wen
    Hongjie, Lei
    Huang Liangkun
    Wen Zhiyu
    [J]. LASER & OPTOELECTRONICS PROGRESS, 2018, 55 (10)
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