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
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2023年 / 62卷 / 14期
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
  • [1] Iridium-Catalyzed Enantioselective C(sp3)-H Borylation of Cyclopropanes with Simple Ether as Directing Groups
    Wang, Wenfang
    Sun, Wei
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2023, 43 (04) : 1605 - 1607
  • [2] Chiral Bidentate Boryl Ligand Enabled Iridium-Catalyzed Enantioselective C(sp3)-H Borylation of Cyclopropanes
    Shi, Yongjia
    Gao, Qian
    Xu, Senmiao
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (27) : 10599 - 10604
  • [3] Aryl Chloride-Directed Enantioselective C(sp2)-H Borylation Enabled by Iridium Catalysis
    Zhao, Hongliang
    Zhao, Chao-Yue
    Chen, Lili
    Xia, Chungu
    Hong, Xin
    Xu, Senmiao
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2023, 145 (46) : 25214 - 25221
  • [4] Iridium-Catalyzed Enantioselective C(sp3)-H Borylation of Aminocyclopropanes
    Shi, Yongjia
    Yang, Yuhuan
    Xu, Senmiao
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (19)
  • [5] Iridium-Catalyzed Enantioselective α-C(sp3)-H Borylation of Azacycles
    Chen, Lili
    Yang, Yuhuan
    Liu, Luhua
    Gao, Qian
    Xu, Senmiao
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (28) : 12062 - 12068
  • [6] Site- and Stereoselective C(sp3)-H Borylation of Strained (Hetero)Cycloalkanols Enabled by Iridium Catalysis
    Gao, Qian
    Xu, Senmiao
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (08)
  • [7] Amide directed iridium C(sp3)-H borylation catalysis with high N-methyl selectivity
    Dannatt, Jonathan E.
    Yadav, Anshu
    Smith, Milton R.
    Maleczka, Robert E., Jr.
    TETRAHEDRON, 2022, 109
  • [8] Iridium-Catalyzed Enantioselective Unbiased Methylene C(sp3)-H Borylation of Acyclic Amides
    Yang, Yuhuan
    Chen, Lili
    Xu, Senmiao
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (07) : 3524 - 3528
  • [9] Iridium-CatalyzedEnantioselective C(sp3)-H Borylation of Cyclobutanes
    Chen, Xiang
    Chen, Lili
    Zhao, Hongliang
    Gao, Qian
    Shen, Zhenlu
    Xu, Senmiao
    CHINESE JOURNAL OF CHEMISTRY, 2020, 38 (12) : 1533 - 1537
  • [10] Pd(II)-Catalyzed Enantioselective C(sp3)-H Borylation
    He, Jian
    Shao, Qian
    Wu, Qingfeng
    Yu, Jin-Quan
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (09) : 3344 - 3347
12345