Synthesis of new amidophosphite ligand and its application in Ir-catalyzed asymmetric hydrogenation of heterocyclic compounds

被引：0
|
作者：
S. E. Lyubimov
D. V. Ozolin
A. A. Pavlov
I. N. Fedorova
V. S. Velezheva
V. A. Davankov
机构：
[1] Russian Academy of Sciences,A. N. Nesmeyanov Institute of Organoelement Compounds
来源：
Russian Chemical Bulletin | 2013年 / 62卷
关键词：
asymmetric hydrogenation; amidophosphite; iridium; heterocyclic compounds;
D O I：
暂无
中图分类号：
学科分类号：
摘要：
A new chiral amidophosphite ligand was synthesized and tested in the iridium-catalyzed hydrogenation of heterocyclic compounds. The enantioselectivity of hydrogenation of 2-methylquinoline considerably increases when piperidine hydrochloride is used as an additive. The hydrogenation reaction of 8-methyl-2,4,5,6-tetrahydro-1H-pyrazino[3,2,1-jk]carbazole by metal complex was conducted for the first time to prepare enantiomerically enriched antidepressant Pyrazidol.
引用
收藏
页码：1405 / 1408
页数：3
相关论文
共 50 条
  • [1] Synthesis of new amidophosphite ligand and its application in Ir-catalyzed asymmetric hydrogenation of heterocyclic compounds
    Lyubimov, S. E.
    Ozolin, D. V.
    Pavlov, A. A.
    Fedorova, I. N.
    Velezheva, V. S.
    Davankov, V. A.
    RUSSIAN CHEMICAL BULLETIN, 2013, 62 (06) : 1405 - 1408
  • [2] The Use of Phosphite-Type Ligands in the Ir-Catalyzed Asymmetric Hydrogenation of Heterocyclic Compounds
    Lyubimov, Sergey E.
    Ozolin, Dmitry V.
    Ivanov, Pavel Yu
    Melman, Artem
    Velezheva, Valeriya S.
    Davankov, Vadim A.
    CHIRALITY, 2014, 26 (01) : 56 - 60
  • [3] Ir-Catalyzed Asymmetric Hydrogenation of -Alkylidene -Lactams and Cyclobutanones
    Xia, Jingzhao
    Nie, Yu
    Yang, Guoqiang
    Liu, Yangang
    Gridnev, Ilya D.
    Zhang, Wanbin
    CHINESE JOURNAL OF CHEMISTRY, 2018, 36 (07) : 612 - 618
  • [4] Ir-catalyzed asymmetric hydrogenation of 3-arylindenones for the synthesis of chiral 3-arylindanones
    Yan, Jun
    Nie, Yu
    Gao, Feng
    Yuan, Qianjia
    Xie, Fang
    Zhang, Wanbin
    TETRAHEDRON, 2021, 84
  • [5] A supramolecularly tunable chiral diphosphine ligand: application to Rh and Ir-catalyzed enantioselective hydrogenation
    Zhang, Xi-Chang
    Hu, Yi-Hu
    Chen, Chuan-Fu
    Fang, Qiang
    Yang, Li-Yao
    Lu, Ying-Bo
    Xie, Lin-Jie
    Wu, Jing
    Li, Shijun
    Fang, Wenjun
    CHEMICAL SCIENCE, 2016, 7 (07) : 4594 - 4599
  • [6] Applications of Phosphoramidite Ligands in Ir-Catalyzed Asymmetric Hydrogenation Reactions
    Yuan, Qianjia
    Zhang, Wanbin
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2016, 36 (02) : 274 - 282
  • [7] Mechanism Studies of Ir-Catalyzed Asymmetric Hydrogenation of Unsaturated Carboxylic Acids
    Li, Mao-Lin
    Yang, Shuang
    Su, Xun-Cheng
    Wu, Hui-Ling
    Yang, Liang-Liang
    Zhu, Shou-Fei
    Zhou, Qi-Lin
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (01) : 541 - 547
  • [8] Asymmetric Ir-catalyzed hydrogenation of 1,5-benzodiazepinones using mixtures of ligands
    Lyubimov, S. E.
    Ozolin, D. V.
    Davankov, V. A.
    RUSSIAN CHEMICAL BULLETIN, 2017, 66 (06) : 1059 - 1061
  • [9] Asymmetric Ir-catalyzed hydrogenation of 1,5-benzodiazepinones using mixtures of ligands
    S. E. Lyubimov
    D. V. Ozolin
    V. A. Davankov
    Russian Chemical Bulletin, 2017, 66 : 1059 - 1061
  • [10] Ir-catalyzed asymmetric hydrogenation of ketones using novel PNO phosphine ligands
    Zhang, Shaoke
    Duan, Yanan
    Zeng, Liyao
    Wen, Jialin
    Zhang, Xumu
    CHINESE SCIENCE BULLETIN-CHINESE, 2021, 66 (25): : 3318 - 3324
12345