Copper-Catalyzed Asymmetric Hydroallylation of Vinylsilanes

被引：10
|
作者：
Wang, Simin [1 ]
Zhang, Qiao [1 ]
Niu, Junbo [1 ]
Guo, Xiaobing [1 ]
Xiong, Tao [1 ]
Zhang, Qian [1 ,2 ]
机构：
[1] Northeast Normal Univ, Dept Chem, Changchun 130024, Peoples R China
[2] Shanghai Inst Organ Chem, State Key Lab Organometall Chem, 345 Lingling Lu, Shanghai 200032, Peoples R China
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 2022卷 / 17期
关键词：
Allylic electrophile; Asymmetric hydroallylation; Chiral silane; CuH catalysis; Vinylsilane; SILICON-STEREOGENIC DIBENZOSILOLES; CARBON QUATERNARY STEREOCENTERS; ALLYLIC SUBSTITUTION-REACTIONS; H BOND INSERTION; ENANTIOSELECTIVE SYNTHESIS; C-H; RECENT PROGRESS; DEHYDROGENATIVE SILYLATION; ORGANOSILICON COMPOUNDS; ALKYLATION REACTIONS;
D O I：
10.1002/ejoc.202101575
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A copper-catalyzed asymmetric hydroallylation of readily available vinylsilanes with allylic phosphates in the presence of hydrosilane was developed. These transformations can be performed under mild reaction conditions and provide the useful chiral organosilanes with good to excellent level of enantiocontrol.
引用
收藏
页数：5
相关论文
共 50 条
  • [1] Asymmetric Synthesis of Borylalkanes via Copper-Catalyzed Enantioselective Hydroallylation
    Han, Jung Tae
    Jang, Won Jun
    Kim, Namhyeon
    Yun, Jaesook
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (46) : 15146 - 15149
  • [2] Asymmetric Synthesis of Silicon-Stereogenic Silanes by Copper-Catalyzed Desymmetrizing Protoboration of Vinylsilanes
    Zhang, Ge
    Li, Yanfei
    Wang, Ying
    Zhang, Qian
    Xiong, Tao
    Zhang, Qian
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (29) : 11927 - 11931
  • [3] Copper-catalyzed hydroallylation of allenes employing hydrosilanes and allyl chlorides
    Fujihara, Tetsuaki
    Yokota, Ken
    Terao, Jun
    Tsuji, Yasushi
    [J]. CHEMICAL COMMUNICATIONS, 2017, 53 (56) : 7898 - 7900
  • [4] Enantioselective Synthesis of α-Aminosilanes by Copper-Catalyzed Hydroamination of Vinylsilanes
    Niljianskul, Nootaree
    Zhu, Shaolin
    Buchwald, Stephen L.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (05) : 1638 - 1641
  • [5] Ligand-Controlled Regiodivergent and Enantioselective Copper-Catalyzed Hydroallylation of Alkynes
    Xu, Guoxing
    Zhao, Haiyan
    Fu, Bin
    Cang, Aijie
    Zhang, Ge
    Zhang, Qian
    Xiong, Tao
    Zhang, Qian
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (42) : 13130 - 13134
  • [6] Synthesis of β-Boryl-α-Aminosilanes by Copper-Catalyzed Aminoboration of Vinylsilanes
    Kato, Kodai
    Hirano, Koji
    Miura, Masahiro
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (46) : 14398 - 14402
  • [7] Fluorinated Vinylsilanes from the Copper-Catalyzed Defluorosilylation of Fluoroalkene Feedstocks
    Sakaguchi, Hironobu
    Ohashi, Masato
    Ogoshi, Sensuke
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (01) : 328 - 332
  • [8] Asymmetric copper-catalyzed alkynylallylic dimethylamination
    Luo, Si-Yuan
    Lin, Guo-Qiang
    He, Zhi-Tao
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (03) : 690 - 695
  • [9] Copper-Catalyzed Highly Regioselective Silylcupration of Terminal Alkynes to Form α-Vinylsilanes
    Wang, Peng
    Yeo, Xue-Liang
    Loh, Teck-Peng
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (05) : 1254 - 1256
  • [10] Stereoselective synthesis of vinylsilanes via copper-catalyzed silylation of alkenes with silanes
    Gu, Jian
    Cai, Chun
    [J]. CHEMICAL COMMUNICATIONS, 2016, 52 (71) : 10779 - 10782
12345