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

被引:18
|
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
  • [41] Enantioselective Remote C(sp3)-H Cyanation via Dual Photoredox and Copper Catalysis
    Chen, Hui
    Jin, Weiwei
    Yu, Shouyun
    ORGANIC LETTERS, 2020, 22 (15) : 5910 - 5914
  • [42] Dehydrogenative B-H/C(sp3)-H Benzylic Borylation within the Coordination Sphere of Platinum(II)
    Kelly, Colin M.
    Fuller, Jack T., III
    Macaulay, Casper M.
    McDonald, Robert
    Ferguson, Michael J.
    Bischof, Steven M.
    Sydora, Orson L.
    Ess, Daniel H.
    Stradiotto, Mark
    Turculet, Laura
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (22) : 6312 - 6316
  • [43] Enantioselective C(sp2)-C(sp3) Bond Construction by Ni Catalysis
    Chen, Li-Ming
    Reisman, Sarah E.
    ACCOUNTS OF CHEMICAL RESEARCH, 2024, 57 (05) : 751 - 762
  • [44] Directed γ-C(sp3)-H Alkylation of Carboxylic Acid Derivatives through Visible Light Photoredox Catalysis
    Chen, Dian-Feng
    Chu, Tjohn C. K.
    Rovis, Tomislav
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (42) : 14897 - 14900
  • [45] Palladium(II)-Catalyzed Directed Trifluoromethylthiolation of Unactivated C(sp3)-H Bonds
    Xiong, Heng-Ying
    Besset, Tatiana
    Cahard, Dominique
    Pannecoucke, Xavier
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (08) : 4204 - 4212
  • [46] Iron-Catalyzed C(Sp3)-H Borylation, Thiolation, and Sulfinylation Enabled by Photoinduced Ligand-to-Metal Charge Transfer
    Tu, Jia-Lin
    Hu, Ao-Men
    Guo, Lin
    Xia, Wujiong
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2023, 145 (13) : 7600 - 7611
  • [47] Ligand-Enabled Palladium(II)-Catalyzed Enantioselective β-C(sp3)-H Arylation of Aliphatic Tertiary Amides
    Yuan, Chen-Hui
    Wang, Xiao-Xia
    Jiao, Lei
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (17)
  • [48] Iridium(I)-Catalyzed α-C(sp3)-H Alkylation of Saturated Azacycles
    Verma, Pritha
    Richter, Jeremy M.
    Chekshin, Nikita
    Qiao, Jennifer X.
    Yu, Jin-Quan
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (11) : 5117 - 5125
  • [49] Mechanistic Insights and the Origin of Regioselective Borylation in an Iridium-Catalyzed Alkyl C(sp3)-H Bond Functionalization
    Patel, Chandan
    Abraham, Vibin
    Sunoj, Raghavan B.
    ORGANOMETALLICS, 2017, 36 (01) : 151 - 158
  • [50] A Computational Mechanistic Study of Pd(II)-Catalyzed Enantioselective C(sp3)-H Borylation: Roles of APAO Ligands
    Xing, Yang-Yang
    Liu, Jian-Biao
    Sun, Qing-Min
    Sun, Chuan-Zhi
    Huang, Fang
    Chen, De-Zhan
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (17) : 10690 - 10700