Chiral phosphoric acid catalyzed aza-Friedel-Crafts alkylation of indoles with cyclic aryl α-ketimino esters

被引：26
|
作者：
Zhao, Yunlong [1 ,2 ]
Wang, Longsheng [1 ]
Zhao, Junling [2 ]
机构：
[1] Hubei Univ Technol, Inst POM Based Mat, Sch Mat & Chem Engn, Wuhan 430068, Hubei Province, Peoples R China
[2] Chinese Acad Sci, Guangzhou Inst Biomed & Hlth, Guangzhou 510530, Guangdong, Peoples R China
来源：
TETRAHEDRON LETTERS | 2017年 / 58卷 / 03期
基金：
中国国家自然科学基金;
关键词：
Organocatalysis; Aza-Friedel-Crafts alkylation; Enantioselective; Indoles; alpha-Ketimino esters; BRONSTED ACID; ENANTIOSELECTIVE ADDITION; ASYMMETRIC-SYNTHESIS; AMINO-ACIDS; N-ACYL; ALKYNYLATION; CONSTRUCTION; IMINES; KETOIMINES; BEARING;
D O I：
10.1016/j.tetlet.2016.12.012
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A highly enantioselective aza-Friedel-Crafts alkylation of indoles with cyclic aryl alpha-ketimino esters catalyzed by a chiral phosphoric acid has been developed, the corresponding alpha,alpha-disubstituted unnatural alpha-amino ester derivatives were obtained in moderate to high yields (67-85%) with high enantioselectivities (up to 93% ee) under mild reaction conditions. (C) 2016 Published by Elsevier Ltd.
引用
收藏
页码：213 / 217
页数：5
相关论文
共 50 条
  • [1] Chiral phosphoric acid-catalyzed enantioselective Aza-Friedel-Crafts reaction of Indoles
    Terada, Masahiro
    Yokoyama, Shigeko
    Sorimachi, Keiichi
    Uraguchi, Daisuke
    ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (11-12) : 1863 - 1867
  • [2] 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
  • [3] 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
  • [4] Enantioselective aza-Friedel-Crafts reaction of cyclic ketimines with indoles using chiral imidazoline-phosphoric acid catalysts
    Nakamura, Shuichi
    Furukawa, Takashi
    Hatanaka, Tsubasa
    Funahashi, Yasuhiro
    CHEMICAL COMMUNICATIONS, 2018, 54 (31) : 3811 - 3814
  • [5] Chiral Phosphoric Acid-Catalyzed Asymmetric Aza-Friedel-Crafts Reaction of Indoles with Cyclic N-Acylketimines: Enantioselective Synthesis of Trifluoromethyldihydroquinazolines
    Zhang, Ke-Feng
    Nie, Jing
    Guo, Ran
    Zheng, Yan
    Ma, Jun-An
    ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (17) : 3497 - 3502
  • [6] CHIRAL PHOSPHORIC ACID CATALYZED ASYMMETRIC FRIEDEL-CRAFTS ALKYLATION OF INDOLES WITH NITROOLEFINS
    Tang, Hong-Ying
    Zhang, Zhong-Biao
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2011, 186 (10) : 2038 - 2046
  • [7] Enantioselective Aza-Friedel-Crafts Reaction of Indoles and Pyrroles Catalyzed by Chiral C1-Symmetric Bis(phosphoric Acid)
    Hatano, Manabu
    Toh, Kohei
    Ishihara, Kazuaki
    ORGANIC LETTERS, 2020, 22 (24) : 9614 - 9620
  • [8] Enantioselective aza-Friedel-Crafts reaction of furan with α-ketimino esters induced by a conjugated double hydrogen bond network of chiral bis(phosphoric acid) catalysts
    Hatano, Manabu
    Okamoto, Haruka
    Kawakami, Taro
    Toh, Kohei
    Nakatsuji, Hidefumi
    Sakakura, Akira
    Ishihara, Kazuaki
    CHEMICAL SCIENCE, 2018, 9 (30) : 6361 - 6367
  • [9] Enantioselective Aza-Friedel-Crafts Reaction of Indoles with Ketimines Catalyzed by Chiral Potassium Binaphthyldisulfonates
    Hatano, Manabu
    Mochizuki, Takuya
    Nishikawa, Keisuke
    Ishihara, Kazuaki
    ACS CATALYSIS, 2018, 8 (01): : 349 - 353
  • [10] Enantioselective Aza-Friedel-Crafts Reaction of Pyrroles with Cyclic N-Sulfimines Catalyzed by Chiral BINOL-Phosphoric Acid
    Choi, Sunyoung
    Kim, Sung-Gon
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2018, 39 (11): : 1340 - 1343
12345