Asymmetric Organocatalysis and Photoredox Catalysis for the -Functionalization of Tetrahydroisoquinolines

被引:30
作者
Hou, Hong [1 ,2 ]
Zhu, Shaoqun [1 ]
Atodiresei, Iuliana [1 ]
Rueping, Magnus [1 ,3 ]
机构
[1] Rhein Westfal TH Aachen, Inst Organ Chem, Landoltweg 1, D-52074 Aachen, Germany
[2] Yangzhou Univ, Sch Chem & Chem Engn, Yangzhou 225009, Jiangsu, Peoples R China
[3] KAUST, Catalysis Ctr KCC, Thuwal 239556900, Saudi Arabia
基金
欧洲研究理事会;
关键词
Cyclic ketones; Tetrahydroisoquinolines; Organocatalysis; Photocatalysis; Alkylation; VISIBLE-LIGHT PHOTOCATALYSIS; TERTIARY-AMINES; COMBINING PHOTOREDOX; DUAL CATALYSIS; COUPLING REACTIONS; METAL; KETONES; ACID; TRANSFORMATIONS; METHODOLOGY;
D O I
10.1002/ejoc.201800117
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The asymmetric -alkylation of tetrahydroisoquinolines with cyclic ketones has been accomplished in the presence of a combined catalytic system consisting of a visible-light photoredox catalyst and a chiral primary amine organocatalyst. The desired products were obtained in good yields, high enantioselectivity, and good to excellent diastereoselectivity. (PC: photoredox cycle, EN: enamine cycle).
引用
收藏
页码:1277 / 1280
页数:4
相关论文
共 68 条
  • [1] Combinations of Aminocatalysts and Metal Catalysts: A Powerful Cooperative Approach in Selective Organic Synthesis
    Afewerki, Samson
    Cordova, Armando
    [J]. CHEMICAL REVIEWS, 2016, 116 (22) : 13512 - 13570
  • [2] Synergistic catalysis: A powerful synthetic strategy for new reaction development
    Allen, Anna E.
    MacMillan, David W. C.
    [J]. CHEMICAL SCIENCE, 2012, 3 (03) : 633 - 658
  • [3] The photophysics of photoredox catalysis: a roadmap for catalyst design
    Arias-Rotondo, Daniela M.
    McCusker, James K.
    [J]. CHEMICAL SOCIETY REVIEWS, 2016, 45 (21) : 5803 - 5820
  • [4] Amine Functionalization via Oxidative Photoredox Catalysis: Methodology Development and Complex Molecule Synthesis
    Beatty, Joel W.
    Stephenson, Corey R. J.
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2015, 48 (05) : 1474 - 1484
  • [5] β-phenylethylamines and the isoquinoline alkaloids
    Bentley, KW
    [J]. NATURAL PRODUCT REPORTS, 2004, 21 (03) : 395 - 424
  • [6] Bergonzini G, 2014, CHEM SCI, V5, P112, DOI [10.1039/C3SC52265B, 10.1039/c3sc52265b]
  • [7] A Comparative Mechanistic Study of Cu-Catalyzed Oxidative Coupling Reactions with N-Phenyltetrahydroisoquinoline
    Boess, Esther
    Schmitz, Corinna
    Klussmann, Martin
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (11) : 5317 - 5325
  • [8] Mechanistic Studies on a Cu-Catalyzed Aerobic Oxidative Coupling Reaction with N-Phenyl Tetrahydroisoquinoline: Structure of Intermediates and the Role of Methanol As a Solvent
    Boess, Esther
    Sureshkumar, Devarajulu
    Sud, Abhishek
    Wirtz, Cornelia
    Fares, Christophe
    Klussmann, Martin
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (21) : 8106 - 8109
  • [9] Brimioulle R., 2015, Angew. Chem, V127, P3944
  • [10] Enantioselective Catalysis of Photochemical Reactions
    Brimioulle, Richard
    Lenhart, Dominik
    Maturi, Mark M.
    Bach, Thorsten
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (13) : 3872 - 3890