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
  • [21] NEUROTROPIC AND PSYCHOTROPIC AGENTS .6. 1-ALKOXYMETHYL-1,3-DIHYDRO-2H-1,4-BENZODIAZEPIN-2-ONES
    KISHIMOTO, T
    MATSUO, M
    UEDA, I
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1982, 30 (04) : 1477 - 1480
  • [22] COMPARATIVE-STUDY ON THE PREPARATION OF C(3)-HYDROXY-1,3-DIHYDRO-2H-1,4-BENZODIAZEPIN-2-ONES
    KOVAC, T
    OKLOBDZIJA, M
    SUNJIC, V
    KAIFEZ, F
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1979, 16 (07) : 1449 - 1454
  • [23] NEW SERIES OF BENZODIAZEPINES - 1-HYDROXYALKYL DERIVATIVES OF 1,3-DIHYDRO-2H-1,4-BENZODIAZEPIN-2-ONES
    TAMAGNONE, GF
    DEMARIA, R
    DEMARCHI, F
    ARZNEIMITTEL-FORSCHUNG/DRUG RESEARCH, 1975, 25 (05): : 720 - 722
  • [24] Circular dichroism studies on chiral 1,3,4,5-tetrahycaro-2H-1,5-benzodiazepin-2-ones
    Khan, KM
    Malik, F
    Hasan, M
    Perveen, S
    Snatzke, G
    Voelter, W
    ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 1995, 50 (12): : 1869 - 1882
  • [25] 1,4-BENZODIAZEPINES AND THEIR DERIVATIVES .2. SYNTHESIS AND PROPERTIES OF SEVERAL 1,3-DIHYDRO-2H-1,4-BENZODIAZEPIN-2-ONES
    ANDRONATI, SA
    BOGATSKI.AV
    VIKHLYAE.YI
    ZHILINA, ZI
    KATS, BM
    KLYGUL, TA
    KHUDYAKO.VN
    CHUMACHE.TK
    ENNAN, AA
    ZHURNAL OBSHCHEI KHIMII, 1970, 40 (08): : 1881 - +
  • [26] QUINAZOLINES AND 1,4-BENZODIAZEPINES .22. A REARRANGEMENT OF 5-PHENYL-1,3-DIHYDRO-2H-1,4-BENZODIAZEPIN-2-ONES
    FRYER, RI
    STERNBACH, LH
    JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (02): : 524 - +
  • [27] SYNTHESES AND CD STUDIES OF OPTICALLY-ACTIVE SUBSTITUTED 1,3,4,5-TETRAHYDRO-2H-1,5-BENZODIAZEPIN-2-ONES
    MALIK, F
    HASAN, M
    KHAN, KM
    PERVEEN, S
    SNATZKE, G
    DUDDECK, H
    VOELTER, W
    LIEBIGS ANNALEN, 1995, (10): : 1861 - 1869
  • [28] A novel approach for the syntheses of 5-methoxycarbonyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one-N4-oxides from N-chloroacetylisatins
    Sirohi, R
    Singh, A
    Shastri, S
    Kishore, D
    JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 2004, 81 (03) : 254 - 257
  • [29] 1,4-BENZODIAZEPINES AND THEIR DERIVATIVES .5. POLAROGRAPHIC REDUCTION AND STRUCTURE OF 1,3-DIHYDRO-2H-1,4-BENZODIAZEPIN-2-ONES AND 2-THIONES
    BOGATSKII, AV
    ANDRONAT.SA
    GULTYAI, VP
    VIKHLYAE.YI
    GALATIN, AF
    ZHILINA, ZI
    KLYGUL, TA
    ZHURNAL OBSHCHEI KHIMII, 1971, 41 (06): : 1358 - +
  • [30] Direct and Enantioselective Synthesis of N-H-Free 1,5-Benzodiazepin-2-ones by an N-Heterocyclic Carbene Catalyzed [3+4] Annulation Reaction
    Fang, Chao
    Cao, Jing
    Sun, Kewen
    Zhu, Jindong
    Lu, Tao
    Du, Ding
    CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (09) : 2103 - +