RETRACTED: Iridium-Catalyzed Asymmetric Borylation of Unactivated Methylene C(sp3)-H Bonds (Retracted article. See vol. 144, pg. 10659, 2019)

被引：67
|
作者：
Reyes, Ronald L. [1 ,2 ]
Iwai, Tomohiro [1 ]
Maeda, Satoshi [1 ,2 ]
Sawamura, Masaya [1 ,2 ]
机构：
[1] Hokkaido Univ, Dept Chem, Fac Sci, Sapporo, Hokkaido 0600810, Japan
[2] Hokkaido Univ, Inst Chem React Design & Discovery WPI ICReDD, Sapporo, Hokkaido 0010021, Japan
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2019年 / 141卷 / 17期
关键词：
ACTIVATION; ENANTIOSELECTIVITY; FUNCTIONALIZATION;
D O I：
10.1021/jacs.9b01952
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Herein, we show the highly enantioselective borylation of unactivated methylene C(sp(3))-H bonds in 2-alkylpyridines and 2-alkyl-1,3-azole derivatives using an iridium-BINOL-based chiral monophosphite catalyst system. Quantum chemical calculations using the artificial force induced reaction (AFIR) method suggested that a monophosphite-Ir-tris(boryl) complex generates a narrow chiral reaction pocket where the differentiation of the enantiotopic methylene C-H bonds is accomplished through an assembly of multiple noncovalent interactions.
引用
收藏
页码：6817 / 6821
页数：5
相关论文
共 50 条
  • [41] RETRACTED: Tripterine ameliorates monosodium urate crystal-induced gouty arthritis by altering macrophage polarization via the miR-449a/NLRP3 axis (Retracted article. See vol. 72, pg. 3, 2023)
    Wang, Yu
    INFLAMMATION RESEARCH, 2021, 70 (03) : 323 - 341
  • [42] RETRACTED: MiR-101 reduces cell proliferation and invasion and enhances apoptosis in endometrial cancer via regulating PI3K/Akt/mTOR (Retracted article. See vol. 30, pg. 275, 2021)
    Zhang, Suxia
    Wang, Min
    Li, Qirong
    Zhu, Ping
    CANCER BIOMARKERS, 2018, 21 (01) : 179 - 186
  • [43] RETRACTED: UM-164: A Potent c-Src/p38 Kinase Inhibitor with In Vivo Activity against Triple-Negative Breast Cancer (Retracted article. See vol. 26, pg. 1777, 2020)
    Gilani, Rabia A.
    Phadke, Sameer
    Bao, Li Wei
    Lachacz, Eric J.
    Dziubinski, Michele L.
    Brandvold, Kristoffer R.
    Steffey, Michael E.
    Kwarcinski, Frank E.
    Graveel, Carrie R.
    Kidwell, Kelley M.
    Merajver, Sofia D.
    Soellner, Matthew B.
    CLINICAL CANCER RESEARCH, 2016, 22 (20) : 5087 - 5096
  • [44] RETRACTED: In vivo and in vitro effects of microRNA-221 on hepatocellular carcinoma development and progression through the JAK-STAT3 signaling pathway by targeting SOCS3 (Retracted article. See vol. 237, pg. 2000, 2022)
    Huang, Shan
    Zhou, Da
    Li, Yu-Xuan
    Ming, Zhi-Yong
    Li, Ke-Zhi
    Wu, Guo-Bin
    Chen, Chuang
    Zhao, Yin-Nong
    JOURNAL OF CELLULAR PHYSIOLOGY, 2019, 234 (04) : 3500 - 3514
  • [45] RETRACTED: IL-6/STAT3 pathway intermediates M1/M2 macrophage polarization during the development of hepatocellular carcinoma (Retracted article. See vol. 123, pg. 1118, 2022)
    Yin, Zi
    Ma, Tingting
    Lin, Ye
    Lu, Xin
    Zhang, Chuanzhao
    Chen, Sheng
    Jian, Zhixiang
    JOURNAL OF CELLULAR BIOCHEMISTRY, 2018, 119 (11) : 9419 - 9432
  • [46] RETRACTED: Betulinic acid downregulates expression of oxidative stress-induced lipoprotein lipase via the PKC/ERK/c-Fos pathway in RAW264.7 macrophages (Retracted article. See vol. 208, pg. 186, 2023)
    Peng, Juan
    Lv, Yun-Cheng
    He, Ping-Ping
    Tang, Yan-Yan
    Xie, Wei
    Liu, Xiang-Yu
    Li, Yuan
    Lan, Gan
    Zhang, Min
    Zhang, Chi
    Shi, Jin-Feng
    Zheng, Xi-Long
    Yin, Wei-Dong
    Tang, Chao-Ke
    BIOCHIMIE, 2015, 119 : 192 - 203
  • [47] RETRACTED: Erinacine Facilitates the Opening of the Mitochondrial Permeability Transition Pore Through the Inhibition of the PI3K/Akt/GSK-3β Signaling Pathway in Human Hepatocellular Carcinoma (Retracted article. See vol. 55, pg. 674, 2021)
    Zhou, Li-Jie
    Mo, Yan-Bo
    Bu, Xuan
    Wang, Jian-Jun
    Bai, Jing
    Zhang, Jun-Wei
    Cheng, Ai-Bin
    Ma, Ji-Hong
    Wang, Yi-Wei
    Xie, Yu-Xi
    CELLULAR PHYSIOLOGY AND BIOCHEMISTRY, 2018, 50 (03) : 851 - 867
  • [48] RETRACTED: MiR-410 affects the proliferation and apoptosis of lung cancer A549 cells through regulation of SOCS3/JAK-STAT signaling pathway (Retracted article. See vol. 24, pg. 11462, 2020)
    Li, M.
    Zheng, R.
    Yuan, F. -L.
    EUROPEAN REVIEW FOR MEDICAL AND PHARMACOLOGICAL SCIENCES, 2018, 22 (18) : 5987 - 5993
  • [49] RETRACTED: The Skp2 Promoter Integrates Signaling through the NF-κB, p53, and Akt/GSK3β Pathways to Regulate Autophagy and Apoptosis (Retracted article. See vol. 55, pg. 342, 2014)
    Barre, Benjamin
    Perkins, Neil D.
    MOLECULAR CELL, 2010, 38 (04) : 524 - 538
  • [50] RETRACTED: myo-Inositol Oxygenase Overexpression Accentuates Generation of Reactive Oxygen Species and Exacerbates Cellular Injury following High Glucose Ambience: A NEW MECHANISM RELEVANT TO THE PATHOGENESIS OF DIABETIC NEPHROPATHY (Retracted article. See vol. 294, pg. 10380, 2019)
    Sun, Lin
    Dutta, Rajesh K.
    Xie, Ping
    Kanwar, Yashpal S.
    JOURNAL OF BIOLOGICAL CHEMISTRY, 2016, 291 (11) : 5688 - 5707
12345