Highly Enantioselective Synthesis of Tetrahydrocarbolines via Iridium-Catalyzed Intramolecular Friedel-Crafts Type Allylic Alkylation Reactions

被引:34
|
作者
Xu, Qing-Long [1 ]
Zhuo, Chun-Xiang [1 ]
Dai, Li-Xin [1 ]
You, Shu-Li [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
KINETIC ASYMMETRIC TRANSFORMATIONS; INDOLES; ALLYLATION; ALCOHOLS; PYRROLES; TETRAHYDROISOQUINOLINES; FUNCTIONALIZATION; DEAROMATIZATION; CONSTRUCTION; ACCESS;
D O I
10.1021/ol4027717
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A highly enantioselective synthesis of substituted tetrahydrocarbolines via Ir-catalyzed Friedel-Crafts type intramolecular asymmetric allylic alkylation of 2-indolyl allyl carbonates has been developed. This strategy features excellent chemoselectivity and enantioselectivity, mild reaction conditions, and an easily accessed chiral ligand.
引用
收藏
页码:5909 / 5911
页数:3
相关论文
共 50 条
  • [21] Iridium-Catalyzed Enantioselective α-Allylic Alkylation of Amides Using Vinyl Azide as Amide Enolate Surrogate
    Chakrabarty, Aditya
    Mukherjee, Santanu
    ORGANIC LETTERS, 2020, 22 (19) : 7752 - 7756
  • [22] Enantioselective synthesis of polycyclic pyrrole derivatives by iridium-catalyzed asymmetric allylic dearomatization and ring-expansive migration reactions
    Huang, Lin
    Xie, Jia-Hao
    Cai, Yue
    Zheng, Chao
    Hou, Xue-Long
    Dai, Li-Xin
    You, Shu-Li
    CHEMICAL COMMUNICATIONS, 2021, 57 (44) : 5390 - 5393
  • [23] Chiral Phosphoric Acid Catalyzed Highly Enantioselective Friedel-Crafts Alkylation Reaction of C3-Substituted Indoles to β,γ-Unsaturated α-Ketimino Esters
    Bi, Bo
    Lou, Qin-Xin
    Ding, Yu-Yang
    Chen, Sheng-Wei
    Zhang, Sha-Sha
    Hu, Wen-Hui
    Zhao, Jun-Ling
    ORGANIC LETTERS, 2015, 17 (03) : 540 - 543
  • [24] Highly Enantioselective Construction of Trifluoromethylated All-Carbon Quaternary Stereocenters via Nickel-Catalyzed Friedel-Crafts Alkylation Reaction
    Gao, Jian-Rong
    Wu, Hao
    Xiang, Bin
    Yu, Wu-Bin
    Han, Liang
    Jia, Yi-Xia
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (08) : 2983 - 2986
  • [25] Enantioselective Synthesis of Tertiary Allylic Fluorides by Iridium-Catalyzed Allylic Fluoroalkylation
    Butcher, Trevor W.
    Hartwig, John F.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (40) : 13125 - 13129
  • [26] Highly Enantioselective Friedel-Crafts Alkylation/N-Hemiacetalization Cascade Reaction with Indoles
    Cheng, Hong-Gang
    Lu, Liang-Qiu
    Wang, Tao
    Yang, Qing-Qing
    Liu, Xiao-Peng
    Li, Yang
    Deng, Qiao-Hui
    Chen, Jia-Rong
    Xiao, Wen-Jing
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (11) : 3250 - 3254
  • [27] Enantioselective Friedel-Crafts Alkylation of Pyrrole with Chalcones Catalyzed by a Dinuclear Zinc Catalyst
    Hua, Yuan-Zhao
    Han, Xing-Wang
    Yang, Xiao-Chao
    Song, Xixi
    Wang, Min-Can
    Chang, Jun-Biao
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (23) : 11690 - 11699
  • [28] Enantioselective Zirconium-Catalyzed Friedel-Crafts Alkylation of Pyrrole with Trifluoromethyl Ketones
    Blay, Gonzalo
    Fernandez, Isabel
    Monleon, Alicia
    Pedro, Jose R.
    Vila, Carlos
    ORGANIC LETTERS, 2009, 11 (02) : 441 - 444
  • [29] Lewis Acid-Catalyzed Enantioselective Friedel-Crafts Alkylation of Pyrrole in Water
    Sun, Jianan
    Gui, Yang
    Huang, Yekai
    Li, Jindong
    Zha, Zhenggen
    Yang, Yu
    Wang, Zhiyong
    ACS OMEGA, 2020, 5 (21): : 11962 - 11970
  • [30] Enantioselective Synthesis of Acyclic α-Quaternary Carboxylic Acid Derivatives through Iridium-Catalyzed Allylic Alkylation
    Shockley, Samantha E.
    Hethcox, J. Caleb
    Stoltz, Brian M.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (38) : 11545 - 11548