Organocatalyzed asymmetric synthesis and absolute configuration assignment of enantioenriched α-benzylaminocoumarins

被引：12
|
作者：
Lin, Hua [1 ]
Tan, Yu [1 ]
Wu, Jian-Ming [1 ]
Yang, Xiao-Di [2 ]
Chen, Jun-Hua [1 ]
Sun, Xing-Wen [1 ]
机构：
[1] Fudan Univ, Dept Chem, Shanghai 200433, Peoples R China
[2] Fudan Univ, Adv Mat Lab, Shanghai 200433, Peoples R China
来源：
TETRAHEDRON LETTERS | 2015年 / 56卷 / 07期
基金：
中国国家自然科学基金;
关键词：
Organocatalysis; Cinchona alkaloid; Mannich reaction; Chiral amine; Coumarin; MANNICH-TYPE REACTION; ENANTIOSELECTIVE SYNTHESIS; COUMARIN DERIVATIVES; CINCHONA ALKALOIDS; ORGANIC CATALYSIS; KETO-ESTERS; EFFICIENT; IMINES; LEVOCETIRIZINE; STEREOCENTERS;
D O I：
10.1016/j.tetlet.2014.12.138
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A cinchona alkaloid catalyzed asymmetric Mannich reaction of 4-hydroxycoumarins and N-p-tolylsulfinylimines was achieved to synthesize enantioenriched alpha-benzylaminocoumarins in moderate to excellent yields (up to 99%) and with moderate to good enantioselectivities (up to 83% ee). The absolute configuration of the resulting chiral amines was assigned by analysis of computational and experimental electronic circular dichroism (ECD) spectroscopies. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码：913 / 917
页数：5
相关论文
共 50 条
  • [1] Asymmetric Synthesis and Absolute Configuration Determination of an Enantioenriched Alcohol: A Discovery-Based Undergraduate Laboratory Experiment
    King, Ryan P.
    Wagner, Alexander J.
    Burtea, Alexander
    King, Susan M.
    JOURNAL OF CHEMICAL EDUCATION, 2020, 97 (03) : 793 - 800
  • [2] Enantioselective Total Synthesis and Absolute Configuration Assignment of (+)-Tronocarpine Enabled by an Asymmetric Michael/Aldol Reaction
    Tan, Dong-Xing
    Zhou, Jie
    Liu, Chao-You
    Han, Fu-She
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (10) : 3834 - 3839
  • [3] Organocatalyzed Asymmetric Synthesis of Morphans
    Bradshaw, Ben
    Parra, Claudio
    Bonjoch, Josep
    ORGANIC LETTERS, 2013, 15 (10) : 2458 - 2461
  • [4] Absolute asymmetric Strecker synthesis in a mixed aqueous medium: reliable access to enantioenriched α-aminonitrile
    Miyagawa, Shinobu
    Aiba, Shohei
    Kawamoto, Hajime
    Tokunaga, Yuji
    Kawasaki, Tsuneomi
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (05) : 1238 - 1244
  • [5] Asymmetric Synthesis of Efavirenz via Organocatalyzed Enantioselective Trifluoromethylation
    Okusu, Satoshi
    Kawai, Hiroyuki
    Yasuda, Yoshimasa
    Sugita, Yutaka
    Kitayama, Takashi
    Tokunaga, Etsuko
    Shibata, Norio
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 3 (04) : 449 - 452
  • [6] Asymmetric organocatalyzed synthesis of coumarin derivatives
    Moreira, Natalia M.
    Martelli, Lorena S. R.
    Correa, Arlene G.
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2021, 17 : 1952 - 1980
  • [7] Catalytic asymmetric synthesis of enantioenriched α-deuterated pyrrolidine derivatives
    Chang, Xin
    Cheng, Xiang
    Wang, Chun-Jiang
    CHEMICAL SCIENCE, 2022, 13 (14) : 4041 - 4049
  • [8] Synthesis of the tetracyclic core of Illicium sesquiterpenes using an organocatalyzed asymmetric Robinson annulation
    Trzoss, Lynnie
    Xu, Jing
    Lacoske, Michelle H.
    Theodorakis, Emmanuel A.
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2013, 9 : 1135 - 1140
  • [9] Asymmetric Organocatalyzed Synthesis of α-Aminophosphinates via Thiourea Anion-Binding Catalysis
    Niland, Caoimhe J.
    Ruddy, Joseph J.
    O'Fearraigh, Martin P.
    Mcgarrigle, Eoghan M.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (11)
  • [10] Intramolecular asymmetric reductive amination: synthesis of enantioenriched dibenz[c,e]azepines
    Yang, Tao
    Guo, Xiaochong
    Yin, Qin
    Zhang, Xumu
    CHEMICAL SCIENCE, 2019, 10 (08) : 2473 - 2477
12345