Palladium-catalyzed ring-forming aminoacetoxylation of alkenes

被引：359
|
作者：
Alexanian, EJ [1 ]
Lee, C [1 ]
Sorensen, EJ [1 ]
机构：
[1] Princeton Univ, Dept Chem, Princeton, NJ 08544 USA
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2005年 / 127卷 / 21期
关键词：
D O I：
10.1021/ja051406k
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A mild, palladium(II)-catalyzed ring-forming aminoacetoxylation of alkenes is described. Treatment of a range of nitrogen nucleophiles with catalytic palladium(II) in the presence of PhI(OAc)2 as oxidant resulted in alkene aminoacetoxylation, affording a variety of nitrogen-containing heterocycles. Our studies indicate the possibility for high levels of reaction regio- and stereocontrol. It appears that this is a stereoselective trans alkene difunctionalization and thus a useful alternative to related cis-selective, metal-catalyzed alkene aminohydroxylation processes. Copyright © 2005 American Chemical Society.
引用
收藏
页码：7690 / 7691
页数：2
相关论文
共 50 条
  • [1] Palladium-catalyzed ring-forming aminoacetoxylation of alkenes
    Alexanian, Erik J.
    Lee, Chulbom
    Sorensen, Erik J.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 230 : U3203 - U3203
  • [2] Palladium-catalyzed ring-forming aminoacetoxylation of alkenes
    Alexanian, Erik J.
    Lee, Chulbom
    Sorensen, Erik J.
    Journal of the American Chemical Society, 2005, 127 (21): : 7690 - 7691
  • [3] Palladium-catalyzed intermolecular aminoacetoxylation of alkenes
    Liu, Guosheng
    Stahl, Shannon S.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233
  • [4] Palladium-Catalyzed Ring-Forming Aminoalkenylation of Alkenes with Aldehydes Initiated by Intramolecular Aminopalladation
    Hu, Yue
    Xie, Yinjun
    Shen, Zhiqiang
    Huang, Hanmin
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (09) : 2473 - 2477
  • [5] Palladium-catalyzed ring-forming reactions: Methods and applications
    Lautens, M
    Alberico, D
    Bressy, C
    Fang, YQ
    Mariampillai, B
    Wilhelm, T
    PURE AND APPLIED CHEMISTRY, 2006, 78 (02) : 351 - 361
  • [6] Palladium-Catalyzed Ring-Forming Alkene Aminoaroylation of Unsaturated Hydrazones and Sulfonamides
    Chen, Jun
    Yang, Meng-Nan
    Chen, Jia-Rong
    Xiao, Wen-Jing
    ORGANIC LETTERS, 2018, 20 (11) : 3314 - 3318
  • [7] Palladium-Catalyzed Intramolecular Aminoacetoxylation of Unactivated Alkenes with Hydrogen Peroxide as Oxidant
    Zhu, Haitao
    Chen, Pinhong
    Liu, Guosheng
    ORGANIC LETTERS, 2015, 17 (06) : 1485 - 1488
  • [8] Palladium-Catalyzed Aerobic Intramolecular Aminoacetoxylation of Alkenes Enabled by Catalytic Nitrate
    Li, Jiaming
    Grubbs, Robert H.
    Stoltz, Brian M.
    ORGANIC LETTERS, 2016, 18 (21) : 5449 - 5451
  • [9] Palladium-catalyzed ring-forming reactions of organic halides with unsaturated substrates and carbon monoxide
    Catellani, M
    Chiusoli, GP
    GAZZETTA CHIMICA ITALIANA, 1996, 126 (02): : 57 - 67
  • [10] Palladium-Catalyzed, Ring-Forming Aromatic C-H Alkylations with Unactivated Alkyl Halides
    Venning, Alexander R. O.
    Bohan, Patrick T.
    Alexanian, Erik J.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (11) : 3731 - 3734
12345