Asymmetric Ir-catalyzed hydrogenation of 4-R-1,3-dihydro-2H-1,5-benzodiazepin-2-ones using a novel phosphoramidite ligand

被引:0
|
作者
S. E. Lyubimov
M. V. Sokolovskaya
I. S. Mikhel
K. P. Birin
V. A. Davankov
机构
[1] Russian Academy of Sciences,A. N. Nesmeyanov Institute of Organoelement Compounds
[2] Russian Academy of Sciences,A. N. Frumkin Institute of Physical Chemistry and Electrochemistry
来源
Russian Chemical Bulletin | 2019年 / 68卷
关键词
asymmetric hydrogenation; phosphoramidites; 1,5-benzodiazepin-2-ones;
D O I
暂无
中图分类号
学科分类号
摘要
A novel chiral phosphoramidite ligand, (Sa)-2-[N-ethyl-N-(1-naphthylmethyl)amino]-dinaphtho[2,1-d:1´,2´-f][1,3,2]dioxaphosphepane, was obtained and tested in Ir-catalyzed asymmetric hydrogenation of a series of 4-R-1,3-dihydro-2H-1,5-benzodiazepin-2-ones, wherein up to 74% ee was achieved. The structure of the resulting compounds was determined based on one- and two-dimensional NMR (1H, 13C, 31P, 1H—1H COSY, 1H—1H ROESY, 1H—13C HSQC and 1H—13C HMBC) spectroscopy data.
引用
收藏
页码:1429 / 1434
页数:5
相关论文
共 50 条
  • [1] Asymmetric Ir-catalyzed hydrogenation of 4-R-1,3-dihydro-2H-1,5-benzodiazepin-2-ones using a novel phosphoramidite ligand
    Lyubimov, S. E.
    Sokolovskaya, M., V
    Mikhel, I. S.
    Birin, K. P.
    Davankov, V. A.
    RUSSIAN CHEMICAL BULLETIN, 2019, 68 (07) : 1429 - 1434
  • [2] Asymmetric Ir-catalyzed hydrogenation of 1,3-dihydro-2H-1,5-benzodiazepin-2-ones using phosphoramidites
    Sokolovskaya, M. V.
    Lyubimov, S. E.
    Mikhel, I. S.
    Birin, K. P.
    Davankov, V. A.
    RUSSIAN CHEMICAL BULLETIN, 2018, 67 (02) : 260 - 264
  • [3] Asymmetric Ir-catalyzed hydrogenation of 1,3-dihydro-2H-1,5-benzodiazepin-2-ones using phosphoramidites
    M. V. Sokolovskaya
    S. E. Lyubimov
    I. S. Mikhel
    K. P. Birin
    V. A. Davankov
    Russian Chemical Bulletin, 2018, 67 : 260 - 264
  • [4] Microwave-Assisted Domino Benzannulation of a-Oxo Ketenes: Preparation of 1,3-Dihydro-2H-1,5-benzodiazepin-2-ones
    Castillo, Juan-Carlos
    Presset, Marc
    Abonia, Rodrigo
    Coquerel, Yoann
    Rodriguez, Jean
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (12) : 2338 - 2345
  • [5] FORMYLATION OF 2,3-DIHYDRO-4-METHYL-1H-1,5-BENZODIAZEPIN-2-ONES
    PROSHKINA, VN
    SOLOMKO, ZF
    BOZHANOVA, NY
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1988, (09): : 1288 - 1288
  • [6] 3-Dimethylaminomethylene-4-phenyl-1,3-dihydro-2H-1,5-benzodiazepin-2-one
    El Rhazi, Abdelouahhab
    Baouid, Abdesselam
    Elhazazi, Said
    Boudina, Aicha
    Essaber, Mohamed
    MOLBANK, 2008, (03)
  • [7] SYNTHESIS OF 4-STYRYL-2,3-DIHYDRO-1H-1,5-BENZODIAZEPIN-2-ONES
    SOLOMKO, ZF
    GAPONOV, AA
    AVRAMENKO, VI
    KHMEL, MP
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1987, (11): : 1560 - 1562
  • [8] Synthesis of 4-pyridyl-2,3-dihydro1h-1,5-benzodiazepin-2-ones
    Bozhanov V.I.
    Ivonin S.P.
    Chemistry of Heterocyclic Compounds, 2002, 38 (09) : 1098 - 1103
  • [9] Enantioselective Synthesis of Chiral 1,5-Benzodiazepin-2-ones by Pd-Catalyzed Asymmetric Hydrogenation and Reductive Amination
    Guo, Qianling
    Xie, Chaochao
    Zi, Guofu
    Hou, Guohua
    ORGANIC LETTERS, 2024, 26 (41) : 8702 - 8707
  • [10] DFT Study on Tautomerism of Dihydro-2H-1,5-benzodiazepin-2-ones and Dihydro-2H-1,5-benzodiazepine-2-thiones
    Okovytyy, Sergiy I.
    Sviatenko, Liudmyla K.
    Gaponov, Alexandr A.
    Kasyan, Liliya I.
    Tarabara, Igor N.
    Leszczynski, Jerzy
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (02) : 280 - 291