Copper-Catalyzed Enantioselective Propargylic Amination of Nonaromatic Propargylic Esters with Amines

被引:60
|
作者
Yoshida, Akiko [1 ]
Hattori, Gaku [1 ]
Miyake, Yoshihiro [1 ]
Nishibayashi, Yoshiaki [1 ]
机构
[1] Univ Tokyo, Sch Engn, Inst Engn Innovat, Bunkyo Ku, Tokyo 1138656, Japan
关键词
SUBSTITUTION-REACTIONS; ASYMMETRIC HYDROGENATION; ALLENYLIDENE COMPLEXES; REDUCTIVE CYCLIZATION; ALCOHOLS; ALDEHYDES; ACETATES; INDOLES;
D O I
10.1021/ol200703g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The enantioselective propargylic amination of propargylic pentafluorobenzoates bearing an alkyl group at the propargylic position with amines in the presence of catalytic amounts of a copper complex and an optically active diphosphine such as BINAP has been found to give the corresponding propargylic amines in good yields with high enantioselectivity.
引用
收藏
页码:2460 / 2463
页数:4
相关论文
共 50 条
  • [41] Nickel-catalyzed Asymmetric Propargylic Amination of Propargylic Carbonates with Aniline Derivatives
    Tsuji, Hiroaki
    Shimizu, Yuka
    Miyazaki, Yusuke
    Kawatsura, Motoi
    CHEMISTRY LETTERS, 2021, 50 (05) : 1002 - 1005
  • [42] Enantioselective Construction of Vicinal Quaternary- Tetrasubstituted Carbon Stereocenters by Copper-Catalyzed Decarboxylative Propargylic Substitution
    You, Yong
    Li, Ting-Ting
    Sun, Ting-Jia
    Zhang, Yan-Ping
    Wang, Zhen-Hua
    Zhao, Jian-Qiang
    Yuan, Wei-Cheng
    ORGANIC LETTERS, 2022, 24 (41) : 7671 - 7676
  • [43] Efficient Synthesis of N-Alkylated 4-Pyridones by Copper-Catalyzed Intermolecular Asymmetric Propargylic Amination
    Shao, Wen
    Wang, Ye
    Yang, Ze-Peng
    Zhang, Xiao
    You, Shu-Li
    CHEMISTRY-AN ASIAN JOURNAL, 2018, 13 (09) : 1103 - 1107
  • [44] Propargylic amines constructed via copper-catalyzed three-component coupling of terminal alkynes, benzal halides and amines
    Lin, Zhewang
    Yu, Dingyi
    Zhang, Yugen
    TETRAHEDRON LETTERS, 2011, 52 (38) : 4967 - 4970
  • [45] Copper-Catalyzed Asymmetric Propargylic Substitution of 2,2,2-Trifluoroethyl-isoxazoles with Propargylic Alcohol Derivatives
    Tian, Guangzheng
    Ji, Mingtong
    Wu, Fan
    Wang, Guan
    Zheng, Changwu
    Wu, Xiaoyu
    ORGANIC LETTERS, 2023, 25 (25) : 4666 - 4671
  • [46] Copper-catalyzed propargylic C-H functionalization for allene syntheses
    Zhang, Dongjie
    Fan, Junjie
    Shi, Yaqi
    Huang, Yankai
    Fu, Chunling
    Wu, Xiaoyan
    Ma, Shengming
    CHEMICAL SCIENCE, 2023, 14 (34) : 9191 - 9196
  • [47] Construction of Chiral Tri- and Tetra-Arylmethanes Bearing Quaternary Carbon Centers: Copper-Catalyzed Enantioselective Propargylation of Indoles with Propargylic Esters
    Tsuchida, Kouhei
    Senda, Yasushi
    Nakajima, Kazunari
    Nishibayashi, Yoshiaki
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (33) : 9728 - 9732
  • [48] Synthesis of Allenamides by Copper-Catalyzed Coupling of Propargylic Bromides and Nitrogen Nucleophiles
    Demmer, Charles S.
    Benoit, Emeline
    Evano, Gwilherm
    ORGANIC LETTERS, 2016, 18 (06) : 1438 - 1441
  • [49] Ruthenium-Catalyzed Enantioselective Propargylic Phosphinylation of Propargylic Alcohols with Phosphine Oxides
    Liu, Shiyao
    Tanabe, Yoshiaki
    Kuriyama, Shogo
    Sakata, Ken
    Nishibayashi, Yoshiaki
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (20) : 11231 - 11236
  • [50] Copper-Catalyzed Oxidative Transformation of Aryl Propargylic Azides to Aryl Propiolonitriles
    Wang, Teng
    Yin, Hang
    Jiao, Ning
    ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (06) : 1207 - 1210