Enantioselective Synthesis of Tetrahydroisoquinolines via Iridium-Catalyzed Intramolecular Friedel-Crafts-Type Allylic Alkylation of Phenols

被引:46
|
作者
Xu, Qing-Long [1 ]
Dai, Li-Xin [1 ]
You, Shu-Li [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
O-ALLYLATION; ASYMMETRIC-SYNTHESIS; CHIRAL CHROMANS; C-ALLYLATION; ETHERIFICATION; COMPLEXES; ALCOHOLS; SUBSTITUTIONS; CARBONATES; BONDS;
D O I
10.1021/ol3008793
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient iridium-catalyzed intramolecular Friedel-Crafts-type allylic alkylation reaction of phenols was developed, affording tetrahydro-isoquinolines with moderate to excellent yields, enantioselectivity, and good regioselectivity.
引用
收藏
页码:2579 / 2581
页数:3
相关论文
共 45 条
  • [1] Enantioselective synthesis of 4-substituted tetrahydroisoquinolines via palladium-catalyzed intramolecular Friedel-Crafts type allylic alkylation of phenols
    Zhao, Zheng-Le
    Xu, Qing-Long
    Gu, Qing
    Wu, Xin-Yan
    You, Shu-Li
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (10) : 3086 - 3092
  • [2] Highly Enantioselective Synthesis of Tetrahydrocarbolines via Iridium-Catalyzed Intramolecular Friedel-Crafts Type Allylic Alkylation Reactions
    Xu, Qing-Long
    Zhuo, Chun-Xiang
    Dai, Li-Xin
    You, Shu-Li
    ORGANIC LETTERS, 2013, 15 (23) : 5909 - 5911
  • [3] Iridium-Catalyzed Asymmetric Intramolecular Allylic Amidation: Enantioselective Synthesis of Chiral Tetrahydroisoquinolines and Saturated Nitrogen Heterocycles
    Teichert, Johannes F.
    Fananas-Mastral, Martin
    Feringa, Ben L.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (03) : 688 - 691
  • [4] Iridium-Catalyzed Intramolecular Asymmetric Allylic Dearomatization of Phenols
    Wu, Qing-Feng
    Liu, Wen-Bo
    Zhuo, Chun-Xiang
    Rong, Zi-Qiang
    Ye, Ke-Yin
    You, Shu-Li
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (19) : 4455 - 4458
  • [5] Palladium-Catalyzed Intramolecular ipso-Friedel-Crafts Allylic Alkylation of Phenols via Arylative Activation of Allenes
    Nemoto, Tetsuhiro
    Nozaki, Tomoyuki
    Yoshida, Mariko
    Hamada, Yasumasa
    ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (13) : 2693 - 2700
  • [6] Iridium-Catalyzed Enantioselective Allylic Alkylation with Functionalized Organozinc Bromides
    Hamilton, James Y.
    Sarlah, David
    Carreira, Erick M.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (26) : 7644 - 7647
  • [7] Enantioselective Synthesis of Vicinal All-Carbon Quaternary Centers via Iridium-Catalyzed Allylic Alkylation
    Hethcox, J. Caleb
    Shockley, Samantha E.
    Stoltz, Brian M.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (28) : 8664 - 8667
  • [8] First asymmetric synthesis of (-)-lintetralin via intramolecular Friedel-Crafts-type cyclization
    Enders, D
    del Signore, G
    Berner, OM
    CHIRALITY, 2003, 15 (06) : 510 - 513
  • [9] Enantioselective Synthesis of Chiral Tetrahydroisoquinolines by Iridium-Catalyzed Asymmetric Hydrogenation of Enamines
    Yan, Pu-Cha
    Xie, Jian-Hua
    Hou, Guo-Hua
    Wang, Li-Xin
    Zhou, Qi-Lin
    ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (18) : 3243 - 3250
  • [10] Stereodivergent synthesis via iridium-catalyzed asymmetric double allylic alkylation of cyanoacetate
    Shen, Chong
    Cheng, Xiang
    Wei, Liang
    Wang, Ruo-Qing
    Wang, Chun-Jiang
    CHEMICAL SCIENCE, 2021, 12 (48) : 15882 - 15891