Enantioselective phosphonation of isoquinolines via chiral phosphoric acid-catalyzed dearomatization

被引：11
|
作者：
Gao, Zhenhua [1 ]
Guo, Yongbiao [1 ]
机构：
[1] State Key Lab NBC Protect Civilian, Beijing, Peoples R China
来源：
CHEMICAL COMMUNICATIONS | 2022年 / 58卷 / 67期
关键词：
ALPHA-AMINO; HYDROPHOSPHONYLATION; LIGANDS; ROUTE;
D O I：
10.1039/d2cc02811e
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An efficient and enantioselective phosphonation protocol for construction of chiral alpha-aminophosphates and alpha-aminodiarylphosphine oxides has been developed based on chiral phosphoric acid-catalyzed dearomatization of isoquinolines. A series of chiral 1,2-dihydroisoquinolines with dimethoxy phosphoryl or diphenylphosphono substituents at the C1-position were constructed with good to excellent yields and enantioselectivities under mild reaction conditions.
引用
收藏
页码：9393 / 9396
页数：4
相关论文
共 50 条
  • [41] Chiral phosphoric acid-catalyzed enantioselective three-component Mannich reaction of acyclic ketones, aldehydes and anilines
    Tong, Shuo
    Wang, Qian
    Wang, Mei-Xiang
    Zhu, Jieping
    TETRAHEDRON, 2018, 74 (38) : 5143 - 5149
  • [42] Chiral Phosphoric Acid-Catalyzed Enantioselective Aza-Friedel-Crafts Alkylation of Indoles with γ-Hydroxy-γ-lactams
    Courant, Thibaut
    Kumarn, Sirirat
    He, Long
    Retailleau, Pascal
    Masson, Geraldine
    ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (05) : 836 - 840
  • [43] Enantioselective Construction of Pyrroloindolines via Chiral Phosphoric Acid Catalyzed Cascade Michael AdditionCyclization of Tryptamines
    Cai, Quan
    Liu, Chuan
    Liang, Xiao-Wei
    You, Shu-Li
    ORGANIC LETTERS, 2012, 14 (17) : 4588 - 4590
  • [44] Chiral Bronsted Acid-Catalyzed Enantioselective α-Hydroxylation of β-Dicarbonyl Compounds
    Lu, Min
    Zhu, Di
    Lu, Yunpeng
    Zeng, Xiaofei
    Tan, Bin
    Xu, Zhenjiang
    Zhong, Guofu
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (13) : 4562 - +
  • [45] Chiral Lewis acid-catalyzed enantioselective Michael reactions in water
    Kobayashi, S
    Kakumoto, K
    Mori, Y
    Manabe, K
    ISRAEL JOURNAL OF CHEMISTRY, 2001, 41 (04) : 247 - 249
  • [46] Chiral Bronsted acid-catalyzed enantioselective addition of indoles to ketimines
    Kano, Taichi
    Takechi, Ryosuke
    Kobayashi, Ryohei
    Maruoka, Keiji
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (05) : 724 - 727
  • [47] Controllable cyclization of alkynyl thioethers via Bronsted acid-catalyzed dearomatization
    Fan, Xin-Yang
    Liu, Xin
    Kong, Yin-Zhu
    Zhu, Bo-Han
    Lin, Jian
    Qian, Peng-Cheng
    Zhou, Bo
    Ye, Long-Wu
    ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (11): : 2766 - 2772
  • [48] Asymmetric Synthesis of Griffipavixanthone Employing a Chiral Phosphoric Acid-Catalyzed Cycloaddition
    Smith, Michael J.
    Reichl, Kyle D.
    Escobar, Randolph A.
    Heavey, Thomas J.
    Coker, David F.
    Schaus, Scott E.
    Porco, John A., Jr.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (01) : 148 - 153
  • [49] Mechanistic Insights into a Chiral Phosphoric Acid-Catalyzed Asymmetric Pinacol Rearrangement
    Falcone, Bruno N.
    Grayson, Matthew N.
    Rodriguez, Juan B.
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (23): : 14683 - 14687
  • [50] Enantioselective synthesis of spirocycles through a chiral phosphoric acid catalyzed desymmetrization
    Minerali, Eni
    Kelley, Amber
    Stingley, Kyla
    Wilent, Jennifer
    Chambers, Nicholas
    Wilson, G. Tyler
    Petersen, Kimberly
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 256
12345