Synthesis of 1,2-amino alcohols via catalytic C-H amidation of sp3 methyl C-H bonds

被引:77
|
作者
Kang, Taek [1 ,2 ]
Kim, Heejeong [1 ,2 ]
Kim, Jeung Gon [1 ,2 ]
Chang, Sukbok [1 ,2 ]
机构
[1] Inst for Basic Sci Korea, Ctr Catalyt Hydrocarbon Functionalizat, Taejon 305701, South Korea
[2] Korea Adv Inst Sci & Technol, Dept Chem, Taejon 305701, South Korea
关键词
ASYMMETRIC AMINOHYDROXYLATION; INTRAMOLECULAR AMIDATION; DIRECTING GROUPS; AMINO-ACIDS; AMINATION; FUNCTIONALIZATION; ACTIVATION; ALKENES; AZIDES; CHEMOSELECTIVITY;
D O I
10.1039/c4cc05655h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Herein a new synthetic route to 1,2-amino alcohols is presented by using C-H amidation of sp(3) methyl C-H bonds as a key step. Readily available alcohols were employed as starting materials after converting them to removable ketoxime chelating groups. Iridium catalysts were found to be effective for the C-H amidation, and LAH reduction was then used to furnish beta-amino alcohol products.
引用
收藏
页码:12073 / 12075
页数:3
相关论文
共 50 条
  • [21] Multifunctionalization of alkenes via aerobic oxynitration and sp3 C-H oxidation
    Taniguchi, Tsuyoshi
    Sugiura, Yuki
    Hatta, Takashi
    Yajima, Atsushi
    Ishibashi, Hiroyuki
    CHEMICAL COMMUNICATIONS, 2013, 49 (22) : 2198 - 2200
  • [22] Direct, Catalytic Monofluorination of sp3 C-H Bonds: A Radical-Based Mechanism with Ionic Selectivity
    Pitts, Cody Ross
    Bloom, Steven
    Woltornist, Ryan
    Auvenshine, Dillon Jay
    Ryzhkov, Lev R.
    Siegler, Maxime A.
    Lectka, Thomas
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (27) : 9780 - 9791
  • [23] Memory of Chirality (MOC) in Intramolecular sp3 C-H Amination
    Mu, Yucheng
    Zhu, Chendan
    Shi, Zhuangzhi
    SYNLETT, 2016, 27 (04) : 486 - 492
  • [24] C-H functionalization of alkenyl SP2 C-H bonds
    Loh, Teck-Peng
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
  • [25] Palladium-Catalyzed Oxidative Carbonylation of Benzylic C-H Bonds via Nondirected C(sp3)-H Activation
    Xie, Pan
    Xie, Yinjun
    Qian, Bo
    Zhou, Han
    Xia, Chungu
    Huang, Hanmin
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (24) : 9902 - 9905
  • [26] Copper-catalyzed aerobic phosphonation of sp3 C-H bonds
    Basle, Olivier
    Li, Chao-Jun
    CHEMICAL COMMUNICATIONS, 2009, (27) : 4124 - 4126
  • [27] Copper(II) Anilides in sp3 C-H Amination
    Jang, Eun Sil
    McMullin, Claire L.
    Kaess, Martina
    Meyer, Karsten
    Cundari, Thomas R.
    Warren, Timothy H.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (31) : 10930 - 10940
  • [28] Iridium-Catalyzed, β-Selective C(sp3)-H Silylation of Aliphatic Amines To Form Silapyrrolidines and 1,2-Amino Alcohols
    Su, Bo
    Lee, Taegyo
    Hartwig, John F.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (51) : 18032 - 18038
  • [29] Copper-catalyzed α-C-H amidation of simple ethers through C(sp3)-H/N-H cross dehydrogenative coupling
    Yue, Qiang
    Xiao, Zhen
    Ran, Ziyao
    Yuan, Songdong
    Zhang, Qian
    Li, Dong
    ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (06): : 967 - 971
  • [30] Rhodium(III)-Catalyzed Amidation of Unactivated C(sp3)H Bonds
    Wang, He
    Tang, Guodong
    Li, Xingwei
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (44) : 13049 - 13052