Highly Efficient Iridium-Catalyzed Asymmetric Hydrogenation of Unprotected β-Enamine Esters

被引:61
|
作者
Hou, Guohua [1 ]
Li, Wei [1 ]
Ma, Miaofeng [1 ]
Zhang, Xiaowei [1 ]
Zhang, Xumu [1 ]
机构
[1] Rutgers State Univ, Dept Chem & Chem Biol & Pharmaceut Chem, Piscataway, NJ 08854 USA
基金
美国国家卫生研究院;
关键词
ACID-DERIVATIVES; ANTAGONIST; LIGANDS;
D O I
10.1021/ja105674y
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A highly efficient and enantioselective hydrogenation of unprotected beta-enamine esters catalyzed by Ir-(S,S)-f-Bi-naphane complex has been developed. This methodology provides straightforward access to free beta-amino acids in high yields with excellent enantioselectivities up to 97% ee and high reactivities (TON > 5000).
引用
收藏
页码:12844 / 12846
页数:3
相关论文
共 50 条
  • [41] Short and Straightforward Enantioselective Synthesis of Both Enantiomers of Mequitazine through Iridium-Catalyzed Asymmetric Hydrogenation of a Nonfunctionalized Cyclic Enamine
    Gauthier, Sebastien
    Larquetoux, Laurent
    Nicolas, Marc
    Ayad, Tahar
    Maillos, Philippe
    Ratovelomanana-Vidal, Virginie
    SYNLETT, 2014, 25 (11) : 1606 - 1610
  • [42] Highly Enantioselective Iridium-Catalyzed Hydrogenation of Conjugated Trisubstituted Enones
    Peters, Bram B. C.
    Jongcharoenkamol, Jira
    Krajangsri, Suppachai
    Andersson, Pher G.
    ORGANIC LETTERS, 2021, 23 (01) : 242 - 246
  • [43] Highly enantioselective iridium-catalyzed hydrogenation of heteroaromatic compounds, quinolines
    Wang, WB
    Lu, SM
    Yang, PY
    Han, XW
    Zhou, YG
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (35) : 10536 - 10537
  • [44] Chiral Polymeric Diamine Ligands for Iridium-Catalyzed Asymmetric Transfer Hydrogenation
    Lin, Yaodong
    Xu, Guangqing
    Tang, Wenjun
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2024, : 27736 - 27744
  • [45] Highly efficient iridium-catalyzed oxidation of organosilanes to silanols
    Lee, Y
    Seomoon, D
    Kim, S
    Han, H
    Chang, S
    Lee, PH
    JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (05): : 1741 - 1743
  • [46] Iridium-Catalyzed Asymmetric Transfer Hydrogenation of Quinolines in Biphasic Systems or Water
    Wang, Lixian
    Lin, Jin
    Xia, Chungu
    Sun, Wei
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (23): : 16641 - 16651
  • [47] On the Mechanism of Iridium-Catalyzed Asymmetric Hydrogenation of Imines and Alkenes: A Theoretical Study
    Hopmann, Kathrin Helen
    Bayer, Annette
    ORGANOMETALLICS, 2011, 30 (09) : 2483 - 2497
  • [48] Iridium-catalyzed asymmetric hydrogenation of racemic α-substituted lactones to chiral diols
    Yang, Xiao-Hui
    Yue, Hai-Tao
    Yu, Na
    Li, Yi-Pan
    Xie, Jian-Hua
    Zhou, Qi-Lin
    CHEMICAL SCIENCE, 2017, 8 (03) : 1811 - 1814
  • [49] Efficient Reduction of Esters to Aldehydes through Iridium-Catalyzed Hydrosilylation
    Cheng, Chen
    Brookhart, Maurice
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (37) : 9422 - 9424
  • [50] Iridium-Catalyzed Asymmetric Hydrogenation of β,γ-Unsaturated γ-Lactams: Scope and Mechanistic Studies
    Yuan, Qianjia
    Liu, Delong
    Zhang, Wanbin
    ORGANIC LETTERS, 2017, 19 (05) : 1144 - 1147