Enantioselective silver-catalyzed propargylation of imines

被引：59
|
作者：
Wisniewska, Hanna M. [1 ]
Jarvo, Elizabeth R. [1 ]
机构：
[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92717 USA
来源：
CHEMICAL SCIENCE | 2011年 / 2卷 / 04期
基金：
美国国家科学基金会;
关键词：
INTRAMOLECULAR HYDROAMINATION; HOMOPROPARGYLIC ALCOHOLS; ALLENYLATION; ALLYLATION; COMPLEXES; ALDEHYDES; REAGENTS;
D O I：
10.1039/c0sc00613k
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A catalytic enantioselective method for the propargylation of aldimines is described. A silver catalyst ligated by a bidentate phoshpine is utilized to provide good yields and high ee's for a variety of substrates. Homopropargylic sulfonamide products undergo facile silver-mediated cyclization to generate 2-pyrrolines, useful intermediates for alkaloid synthesis.
引用
收藏
页码：807 / 810
页数：4
相关论文
共 50 条
  • [41] Silver-Catalyzed Chlorination of Aromatic Compounds
    Li Binhua
    Cheng Xiaomin
    Li Chaozhong
    [J]. CHINESE JOURNAL OF CHEMISTRY, 2011, 29 (12) : 2809 - 2812
  • [42] Silver-Catalyzed Stereoselective Aminosulfonylation of Alkynes
    Ning, Yongquan
    Ji, Qinghe
    Liao, Peiqiu
    Anderson, Edward A.
    Bi, Xihe
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (44) : 13805 - 13808
  • [43] Tunable silver-catalyzed nitrene transfer
    Huang, Minxue
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 256
  • [44] Study of silver-catalyzed epoxidation.
    Stacchiola, DJ
    Tysoe, WT
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 219 : U547 - U547
  • [45] Silver-Catalyzed Decarboxylative Alkylfluorination of Alkenes
    Li, Chen-Guang
    Xie, Qiang
    Xu, Xiao-Lan
    Wang, Feng
    Huang, Bei
    Liang, Yu-Feng
    Xu, Hua-Jian
    [J]. ORGANIC LETTERS, 2019, 21 (20) : 8496 - 8500
  • [46] ROLE OF SILVER(II) IN SILVER-CATALYZED OXIDATIONS BY PEROXYDISULFATE
    WALLING, C
    CAMAIONI, DM
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (17): : 3266 - 3271
  • [47] Silver-Catalyzed Hydrogenation of Aldehydes in Water
    Jia, Zhenhua
    Zhou, Feng
    Liu, Mingxin
    Li, Xingshu
    Chan, Albert S. C.
    Li, Chao-Jun
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (45) : 11871 - 11874
  • [48] Silver-Catalyzed Dibromotrifluoromethoxylation of Terminal Alkynes
    Wang, Feng
    Guo, Yuecong
    Zhang, Yutong
    Tang, Pingping
    [J]. ACS CATALYSIS, 2021, 11 (06) : 3218 - 3223
  • [49] Chemoselective and tunable silver-catalyzed aminations
    Schomaker, Jennifer M.
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 247
  • [50] Chiral Bronsted Acid Catalyzed Enantioselective Propargylation of Aldehydes with Allenylboronate
    Reddy, Leleti Rajender
    [J]. ORGANIC LETTERS, 2012, 14 (04) : 1142 - 1145
12345