Enantioselective Copper-Catalyzed Decarboxylative Propargylic Alkylation of Propargylic Esters with β-Keto Acids

被引：51
|
作者：
Zhu, Fu-Lin [1 ,2 ]
Wang, Ya-Hui [1 ]
Zhang, De-Yang [1 ,2 ]
Hu, Xin-Hu [1 ]
Chen, Song [1 ]
Hou, Chuan-Jin [1 ,3 ]
Xu, Jie [1 ]
Hu, Xiang-Ping [1 ]
机构：
[1] Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China
[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
[3] Dalian Polytech Univ, Dalian 116034, Peoples R China
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2014年 / 356卷 / 14-15期
关键词：
asymmetric catalysis; copper; decarboxylative propargylic alkylation; beta-keto acids; propargylic esters; CONJUGATE ADDITION; SUBSTITUTION-REACTIONS; 3-HYDROXY OXINDOLES; TERMINAL ALKYNES; MANNICH REACTION; KETOACIDS; ACETATES; AMINATION; ALCOHOLS; AMINES;
D O I：
10.1002/adsc.201400218
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
The first copper-catalyzed intermolecular enantioselective decarboxylative propargylic alkylation of propargylic esters with beta-keto acids as surrogates of ketones has been successfully developed by using a ketimine P, N, N-ligand. High yields and excellent enantioselectivities (up to 98% ee) have been achieved under the mild reaction conditions.
引用
收藏
页码：3231 / 3236
页数：6
相关论文
共 50 条
  • [41] Cooperative Catalytic Reactions Using Distinct Transition-Metal Catalysts: Ruthenium- and Copper-Catalyzed Enantioselective Propargylic Alkylation
    Ikeda, Masahiro
    Miyake, Yoshihiro
    Nishibayashi, Yoshiaki
    CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (11) : 3321 - 3328
  • [42] Copper-Catalyzed Intermolecular Asymmetric Propargylic Dearomatization of Indoles
    Shao, Wen
    Li, He
    Liu, Chuan
    Liu, Chen-Jiang
    You, Shu-Li
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (26) : 7684 - 7687
  • [43] Copper-Catalyzed Asymmetric Allylic Alkylation of -Keto Esters with Allylic Alcohols
    Trillo, Paz
    Baeza, Alejandro
    ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (10) : 1735 - 1741
  • [44] Cooperative Catalytic Reactions Using Organocatalysts and Transition Metal Catalysts: Enantioselective Propargylic Alkylation of Propargylic Esters with Aldehydes
    Yoshida, Akiko
    Ikeda, Masahiro
    Hattori, Gaku
    Miyake, Yoshihiro
    Nishibayashi, Yoshiaki
    ORGANIC LETTERS, 2011, 13 (04) : 592 - 595
  • [45] Copper-Catalyzed Decarboxylative Alkylation of Terminal Alkynes
    Ye, Changqing
    Li, Yajun
    Bao, Hongli
    ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (21) : 3720 - 3724
  • [46] Copper-Catalyzed Asymmetric Propargylic Alkylation with Oxindoles: Diastereo- and Enantioselective Construction of Vicinal Tertiary and All-Carbon Quaternary Stereocenters
    Xia, Jin-Tao
    Hu, Xiang-Ping
    ORGANIC LETTERS, 2020, 22 (03) : 1102 - 1107
  • [47] Copper-catalyzed intermolecular asymmetric propargylic dearomatization of phenol derivatives
    Shao, Long
    Hu, Xiang-Ping
    CHEMICAL COMMUNICATIONS, 2017, 53 (58) : 8192 - 8195
  • [48] Photoinduced Copper-Catalyzed Monofluoroalkylation of Terminal Alkynes to Propargylic Fluorides
    Hu, Duo-Duo
    Li, Chao
    Gao, Qian
    Nie, Tian-Mei
    Zhang, Kai-Fan
    Wu, Bing-Bing
    Li, Yan
    Wang, Xi-Sheng
    ORGANIC LETTERS, 2023, 25 (24) : 4514 - 4519
  • [49] Synthesis of ( S )-Nyasol through a Copper-Catalyzed Propargylic Substitution
    Kobayashi, Yuichi
    Hirotsu, Takayuki
    SYNLETT, 2023, 34 (02) : 159 - 162
  • [50] Asymmetric copper-catalyzed propargylic amination with amine hydrochloride salts
    Huang, Jian
    Kong, Han-Han
    Li, Si-Jia
    Zhang, Rui-Jin
    Qian, Hao-Dong
    Li, Dan-Ran
    He, Jin-Yu
    Zheng, Yi-Nuo
    Xu, Hao
    CHEMICAL COMMUNICATIONS, 2021, 57 (38) : 4674 - 4677
12345