Simple Ether-Directed Enantioselective C(sp3) H Borylation of Cyclopropanes Enabled by Iridium Catalysis

被引:12
|
作者
Xie, Tian [1 ,2 ]
Chen, Lili [2 ]
Shen, Zhenlu [1 ]
Xu, Senmiao [2 ]
机构
[1] Zhejiang Univ Technol, Coll Chem Engn, Hangzhou 310014, Peoples R China
[2] Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China
基金
中国国家自然科学基金; 国家重点研发计划;
关键词
Asymmetric Catalysis; C-H Borylation; Chiral Bidentate Boryl Ligand; Cyclopropane; Synthetic Method; SIMMONS-SMITH REACTION; ALLYLIC ALCOHOLS; FUNCTIONALIZATION; SILYLATION; ACTIVATION; ACCESS;
D O I
10.1002/anie.202300199
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Reported here is an efficient and simple ether-directed iridium-catalyzed enantioselective C(sp(3)) H borylation of cyclopropanes. Various functional groups were well-tolerated, affording a vast array of chiral cyclopropanes with high enantioselectivities. We also demonstrated that the turnover numbers of the current reaction could be up to 335.
引用
收藏
页数:5
相关论文
共 50 条
  • [21] Selenium-Directed ortho-C-H Borylation by Iridium Catalysis
    Tang, Jia
    Singh, Thishana
    Li, Xingzhen
    Liu, Linpeng
    Zhou, Taigang
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (18): : 11959 - 11967
  • [22] Iridium-Catalyzed Regio- and Enantioselective Borylation of Unbiased Methylene C(sp3)-H Bonds at the Position β to a Nitrogen Center
    Du, Rongrong
    Liu, Luhua
    Xu, Senmiao
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (11) : 5843 - 5847
  • [23] Theoretical Insight into Catalysis of the Aluminabenzene-Iridium Complex for C(sp3)-H Borylation of NEt3: How to Control α- and β-Regioselectivities?
    Zhong, Rong-Lin
    Suzuki, Katsunori
    Yamashita, Makoto
    Sakaki, Shigeyoshi
    ACS CATALYSIS, 2022, 12 (09) : 4880 - 4897
  • [24] Iridium-Catalyzed sp3 C-H Borylation in Hydrocarbon Solvent Enabled by 2,2′-Dipyridylarylmethane Ligands
    Jones, Margaret R.
    Fast, Caleb D.
    Schley, Nathan D.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (14) : 6488 - 6492
  • [25] Accessing phosphine boronates by C(sp2)-H and C(sp3)-H borylation using a cationic iridium complex
    Morris, Kelsey
    Richardson-Solorzano, Stephanie
    Wright, Shawn
    Stewart, Tiffany
    Wilson, Joshua
    Miller, Christopher
    Clark, Timothy
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 257
  • [26] Stereoselective benzylic C(sp3)-H alkenylation enabled by metallaphotoredox catalysis
    Li, Yantao
    Bai, Haonan
    Gao, Qi
    Liu, Kai
    Han, Jie
    Li, Weipeng
    Zhu, Chengjian
    Xie, Jin
    CHEMICAL SCIENCE, 2024, 15 (31) : 12511 - 12516
  • [27] Biocatalytic enantioselective C(sp3)-H fluorination enabled by directed evolution of non-haem iron enzymes
    Zhao, Liu-Peng
    Mai, Binh Khanh
    Cheng, Lida
    Gao, Fangqiu
    Zhao, Yunlong
    Guo, Rui
    Wu, Hao
    Zhang, Yongda
    Liu, Peng
    Yang, Yang
    NATURE SYNTHESIS, 2024, 3 (08): : 967 - 975
  • [28] Dipyridylmethane derivatives as ligands for highly efficient iridium catalyzed sp3 C-H borylation
    Jones, Margaret
    Schley, Nathan
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 258
  • [29] Site- and Enantioselective Homobenzylic C(sp3)-H Borylation via Dehydrogenation of Alkyl Chains
    Tao, Renqing
    Liu, Guixia
    Huang, Zheng
    ORGANIC LETTERS, 2024, 26 (36) : 7626 - 7631
  • [30] Intermolecular Enantioselective Benzylic C(sp3)-H Amination by Cationic Copper Catalysis
    Dai, Ling
    Chen, Ying-Ying
    Xiao, Li-Jun
    Zhou, Qi-Lin
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (24)