Enantioselective Reduction of 3-Substituted Quinolines with a Cyclopentadiene-Based Chiral Bronsted Acid

被引：21
|
作者：
Zhao, Xiaofang [1 ,2 ]
Xiao, Jianliang [1 ,2 ,3 ]
Tang, Weijun [1 ,2 ]
机构：
[1] Shaanxi Normal Univ, Minist Educ, Key Lab Appl Surface & Colloid Chem, Xian 710119, Peoples R China
[2] Shaanxi Normal Univ, Sch Chem & Chem Engn, Xian 710119, Peoples R China
[3] Univ Liverpool, Dept Chem, Liverpool L69 7ZD, Merseyside, England
来源：
SYNTHESIS-STUTTGART | 2017年 / 49卷 / 14期
基金：
美国国家科学基金会;
关键词：
tetrahydroquinolines; transfer hydrogenation; 3-substituted quinolones; enantioselectivity; chiral Bronsted acid; ASYMMETRIC TRANSFER HYDROGENATION; IRIDIUM-CATALYZED HYDROGENATION; 2 CONTIGUOUS STEREOCENTERS; KINETIC RESOLUTION; HETEROAROMATIC-COMPOUNDS; BISPHOSPHINE LIGANDS; DERIVATIVES; TETRAHYDROQUINOLINES; COMPLEXES; EFFICIENT;
D O I：
10.1055/s-0036-1589012
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Enantioselective reduction of 3-substituted quinolines has been achieved using a cyclopentadiene-based chiral Bronsted acid as catalyst and Hantzsch ester as hydrogen donor, affording the corresponding tetrahydroquinolines in good enantioselectivities.
引用
收藏
页码：3157 / 3164
页数：8
相关论文
共 50 条
  • [1] Chiral Catalyst Design: Cyclopentadiene-Based Bronsted Acids
    Fleischer, Ivana
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (27) : 7582 - 7584
  • [2] Chiral Bronsted acid catalyzed enantioselective intermolecular desymmetrizations of 3-substituted azetidines
    Wang, Zhaobin
    Sun, Jianwei
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
  • [3] Highly Enantioselective Synthesis of Cyclic Aminals with a Cyclopentadiene-Based Chiral Carboxylic Acid
    Sui, Yuebo
    Cui, Peng
    Liu, Sensheng
    Zhou, Yanmei
    Du, Peng
    Zhou, Haifeng
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (02) : 215 - 218
  • [4] Cyclopentadiene-based Bronsted acid as a new generation of organocatalyst for transfer hydrogenation of 2-substituted quinoline derivatives
    Qiao, Xiang
    El-Shahat, Mahmoud
    Ullah, Bakhtar
    Bao, Zongbi
    Xing, Huabin
    Xiao, Li
    Ren, Qilong
    Zhang, Zhiguo
    TETRAHEDRON LETTERS, 2017, 58 (21) : 2050 - 2053
  • [5] Chiral Bronsted acid-catalyzed asymmetric transformations of 3-substituted 3-hydroxyisoindolinones
    Gredicak, Matija
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 256
  • [6] Chiral bifunctional organocatalysts for enantioselective synthesis of 3-substituted isoindolinones
    Hu, Xiao-Mu
    Zhang, Rui
    Dong, Hai
    Jia, Yan-Yan
    Bao, Guo-Qiang
    Wang, Ping-An
    RSC ADVANCES, 2023, 13 (35) : 24460 - 24465
  • [7] An enantioselective synthesis of isoquinuclidines from 3-substituted chiral pyridinium salts
    dos Santos, DC
    Gil, RPD
    Gil, L
    Marazano, C
    TETRAHEDRON LETTERS, 2001, 42 (35) : 6109 - 6111
  • [8] Enantioselective Bronsted acid catalysis with chiral cyclopentadienes
    Gheewala, Chirag
    Collins, Bridget
    Lambert, Tristan
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 253
  • [9] THE IONIZATION CONSTANTS OF 3-SUBSTITUTED PYRIDINES, 3-SUBSTITUTED QUINOLINES AND 4-SUBSTITUTED ISOQUINOLINES
    BRYSON, A
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (18) : 4871 - 4876
  • [10] Chiral Bronsted acid-catalyzed diastereo- and enantioselective synthesis of CF3-substituted aziridines
    Chai, Zhuo
    Bouillon, Jean-Philippe
    Cahard, Dominique
    CHEMICAL COMMUNICATIONS, 2012, 48 (76) : 9471 - 9473
12345