Enantioselective Synthesis of Cyclobutylboronates via a Copper-Catalyzed Desymmetrization Approach

被引:96
|
作者
Guisan-Ceinos, Manuel [1 ]
Parra, Alejandro [1 ]
Martin-Heras, Victor [1 ]
Tortosa, Mariola [1 ]
机构
[1] Univ Autonoma Madrid, Madrid, Spain
基金
欧洲研究理事会;
关键词
asymmetric catalysis; boron; copper; cyclobutanes; cyclobutenes; COPPER(I)-CATALYZED REACTION; CYCLOBUTANE DERIVATIVES; 2+2 PHOTOCYCLOADDITIONS; HYDROBORATION; ARYL; LIGANDS; DIPHOSPHINITE; CYCLOADDITION; VINYLARENES; ALKENES;
D O I
10.1002/anie.201601976
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The first catalytic enantioselective synthesis of cyclobutylboronates, by using a chiral copper(I) complex, is reported. A broad variety of cyclobutanes have been prepared with consistently high levels of diastereo- and enantiocontrol. Moreover, this method constitutes the first report of an enantioselective desymmetrization of meso-cyclobutenes to prepare chiral cyclobutanes.
引用
收藏
页码:6969 / 6972
页数:4
相关论文
共 50 条
  • [1] Copper-Catalyzed Enantioselective Synthesis of Oxazolines from Aminotriols via Asymmetric Desymmetrization
    Yamamoto, Kosuke
    Tsuda, Yutaro
    Kuriyama, Masami
    Demizu, Yosuke
    Onomura, Osamu
    CHEMISTRY-AN ASIAN JOURNAL, 2020, 15 (06) : 840 - 844
  • [3] Copper-Catalyzed Diastereo- and Enantioselective Desymmetrization of Cyclopropenes: Synthesis of Cyclopropylboronates
    Parra, Alejandro
    Amenos, Laura
    Guisan-Ceinos, Manuel
    Lopez, Aurora
    Garcia Ruano, Jose Luis
    Tortosa, Mariola
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (45) : 15833 - 15836
  • [4] Research Progress on Copper-Catalyzed Enantioselective Desymmetrization of Diols
    Yu Zhanglong
    Li Zhongliang
    Yang Changjiang
    Gu Qiangshuai
    Liu Xinyuan
    ACTA CHIMICA SINICA, 2023, 81 (08) : 955 - 966
  • [5] Asymmetric Synthesis of Remote Quaternary Centers by Copper-Catalyzed Desymmetrization: An Enantioselective Total Synthesis of (+)-Mesembrine
    Bokka, Apparao
    Mao, James X.
    Hartung, John
    Martinez, Steven R.
    Simanis, Justin A.
    Nam, Kwangho
    Jeon, Junha
    Shen, Xiaoqiang
    ORGANIC LETTERS, 2018, 20 (17) : 5158 - 5162
  • [6] Asymmetric Synthesis of Borylalkanes via Copper-Catalyzed Enantioselective Hydroallylation
    Han, Jung Tae
    Jang, Won Jun
    Kim, Namhyeon
    Yun, Jaesook
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (46) : 15146 - 15149
  • [7] Copper-Catalyzed Enantioselective Arylative Desymmetrization of Prochiral Cyclopentenes with Diaryliodonium Salts
    Wu, Hua
    Wang, Qian
    Zhu, Jieping
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (10) : 2721 - 2725
  • [8] Enantioselective Synthesis of Cyclobutylboronates
    Yuan, Fushan
    Yan, Xufei
    Xia, Ying
    SYNLETT, 2024,
  • [9] Chiral Indoline Synthesis via Enantioselective Intramolecular Copper-Catalyzed Alkene Hydroamination
    Turnpenny, Benjamin W.
    Hyman, Kiante L.
    Chemler, Sherry R.
    ORGANOMETALLICS, 2012, 31 (22) : 7819 - 7822
  • [10] Enantioselective synthesis of γ-chiral amides via copper-catalyzed reductive relay hydroaminocarbonylation
    Yuan, Yang
    Zhang, Youcan
    Wu, Xiao-Feng
    NATURE COMMUNICATIONS, 2024, 15 (01)