Lewis Acid Catalyzed Intramolecular Direct Ene Reaction of Indoles

被引：116
|
作者：
Han, Bo [1 ]
Xiao, You-Cai [1 ]
Yao, Yuan [1 ]
Chen, Ying-Chun [1 ,2 ]
机构：
[1] Sichuan Univ, Key Lab Drug Targeting & Drug Delivery Syst, Educ Minist, Dept Med Chem,W China Sch Pharm, Chengdu 610041, Peoples R China
[2] Sichuan Univ, State Key Lab Biotherapy, W China Hosp, Chengdu 610041, Peoples R China
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2010年 / 49卷 / 52期
关键词：
alkylation; dienamine catalysis; imino-ene reactions; indoles; Lewis acids; FRIEDEL-CRAFTS ALKYLATION; DIELS-ALDER REACTION; ALPHA; BETA-UNSATURATED ALDEHYDES; ALLYLIC ALKYLATION; ALPHA-ALKYLATION; ALLYLATION; FUNCTIONALIZATION; CONSTRUCTION; CYCLIZATIONS; ANNULATION;
D O I：
10.1002/anie.201005296
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
How to fuse heterocycles: The direct enamine-imine isomerization of indoles and subsequent intramolecular imino-ene has been observed under Lewis acid catalysis. This unique reaction occurred for indoles that contain a tethered olefin functionality, and led to fused indoline heterocycles with excellent diastereocontrol (see scheme). Copyright © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：10189 / 10191
页数：3
相关论文
共 50 条
  • [31] Chiral Lewis-acid catalyzed carbonyl-ene reactions
    Hutson, Gerri
    Rawal, Viresh H.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233
  • [32] CHANGES IN ENE REACTION-MECHANISMS WITH LEWIS ACID CATALYSIS
    STEPHENSON, LM
    ORFANOPOULOS, M
    JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (10): : 2200 - 2201
  • [33] LEWIS ACID-CATALYZED ENE REACTIONS OF ETHYNYL PARATOLYL SULFONE
    SNIDER, BB
    KIRK, TC
    ROUSH, DM
    GONZALEZ, D
    JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (25): : 5015 - 5017
  • [34] Lewis Acid Catalyzed Reaction of Triphenylmethanol with Acetylacetone
    Konshin, Valery
    Turmasova, Anna
    Konshina, Dzhamilya
    LETTERS IN ORGANIC CHEMISTRY, 2015, 12 (07) : 511 - 515
  • [35] Lewis Acid-Catalyzed Carbonyl-Ene Reaction: Interplay between Aromaticity, Synchronicity, and Pauli Repulsion
    Rodriguez, Humberto A.
    Cruz, Daniel A.
    Padron, Juan I.
    Fernandez, Israel
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (15): : 11102 - 11110
  • [36] Intramolecular dihydrogen bond A new perspective in Lewis acid catalyzed nucleophilic epoxide ring opening reaction
    Dixit, Vaibhav A.
    Rathi, Prakash C.
    Bharatam, Prasad V.
    JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM, 2010, 962 (1-3): : 97 - 100
  • [37] Ruthenium-Catalyzed Intramolecular Allylic Dearomatization/Migration Reaction of Indoles and Pyrroles
    Yang, Ze-Peng
    Zhuo, Chun-Xiang
    You, Shu-Li
    ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (08) : 1731 - 1734
  • [38] Pd-Catalyzed Asymmetric Intramolecular Dearomatizing Reductive Heck Reaction of Indoles
    Wang, Bi
    Gao, Jing-Kun
    Sun, Shuo
    Shen, Zhen-Lu
    Yang, Yun-Fang
    Liang, Ren-Xiao
    Jia, Yi-Xia
    ORGANIC LETTERS, 2024, 26 (18) : 3739 - 3743
  • [39] Lewis Acid-Catalyzed Diastereoselective Domino Reaction of Ene-Ynamide with Trimethylsilyl Cyanide to Construct Spiroindolines
    Yamaoka, Yousuke
    Yamasaki, Daisuke
    Kajiwara, Daigo
    Shinozaki, Makiko
    Yamada, Ken-ichi
    Takasu, Kiyosei
    ORGANIC LETTERS, 2022, 24 (24) : 4389 - 4393
  • [40] Palladium-catalyzed intramolecular diastereoselective dearomatization reaction of indoles with: N -tosylhydrazones
    Duan, Shao-Bo
    Zhang, Hong-Yu
    Hao, Bo-Ya
    Zhao, Jiquan
    Han, Ya-Ping
    Zhang, Yuecheng
    Liang, Yong-Min
    Organic Chemistry Frontiers, 2021, 8 (20) : 5895 - 5901
12345