Highly efficient synthesis of chiral aromatic ketones via Rh-catalyzed asymmetric hydrogenation of β,β-disubstituted enones

被引:22
|
作者
Zhang, Tao [1 ]
Jiang, Jun [2 ]
Yao, Lin [3 ]
Geng, Huiling [1 ]
Zhang, Xumu [4 ]
机构
[1] Northwest A&F Univ, Sch Pharm & Chem, Yangling 712100, Shaanxi, Peoples R China
[2] Wuhan Univ, Coll Chem & Mol Sci, Wuhan 430072, Hubei, Peoples R China
[3] Fourth Mil Med Univ, Sch Chem & Pharm, Xian 710032, Shaanxi, Peoples R China
[4] South Univ Sci & Technol, Dept Chem, Guangzhou 518055, Guangdong, Peoples R China
基金
中国国家自然科学基金;
关键词
CONJUGATE ADDITION; ALPHA; BETA-UNSATURATED KETONES; THIOUREA; LIGANDS; 1,4-ADDITION; DIETHYLZINC; REDUCTION; COMPLEXES;
D O I
10.1039/c7cc04045h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A succinct and efficient protocol was developed for the synthesis of chiral aromatic ketones via asymmetric hydrogenation of beta,beta-disubstituted enones with rhodium catalysts based on chiral bisphosphine thiourea ligands. A series of substrates (17 examples) was smoothly catalyzed to afford the corresponding chiral aromatic ketones in high conversions (>99%) with excellent enantioselectivities (up to 96% ee).
引用
收藏
页码:9258 / 9261
页数:4
相关论文
共 50 条
  • [31] First chiral phosphite with a quaternary ammonium fragment: Synthesis and use in Rh-catalyzed asymmetric hydrogenation
    S. E. Lyubimov
    V. A. Davankov
    P. M. Valetskii
    P. V. Petrovskii
    M. G. Maksimova
    K. N. Gavrilov
    Russian Chemical Bulletin, 2006, 55 : 1448 - 1451
  • [32] First chiral phosphite with a quaternary ammonium fragment: synthesis and use in Rh-catalyzed asymmetric hydrogenation
    Lyubimov, S. E.
    Davankova, V. A.
    Valelskii, P. M.
    Petrovskii, P. V.
    Maksimova, M. G.
    Gavrilov, K. N.
    RUSSIAN CHEMICAL BULLETIN, 2006, 55 (08) : 1448 - 1451
  • [33] Highly Enantioselective Synthesis of Chiral Succinimides via Rh/Bisphosphine-Thiourea-Catalyzed Asymmetric Hydrogenation
    Han, Zhengyu
    Li, Pan
    Zhang, Zongpeng
    Chen, Caiyou
    Wang, Qian
    Dong, Xiu-Qin
    Zhang, Xumu
    ACS CATALYSIS, 2016, 6 (09): : 6214 - 6218
  • [34] Asymmetric synthesis of chiral Roche ester and its derivatives via Rh-catalyzed enantioselective hydrogenation with chiral phosphine-phosphoramidite ligands
    Qiu, Min
    Wang, Dao-Yong
    Hu, Xiang-Ping
    Huang, Jia-Di
    Yu, Sai-Bo
    Deng, Jun
    Duan, Zheng-Chao
    Zheng, Zhuo
    TETRAHEDRON-ASYMMETRY, 2009, 20 (02) : 210 - 213
  • [35] Rh-Catalyzed One-Pot Sequential Asymmetric Hydrogenation of α-Dehydroamino Ketones for the Synthesis of Chiral Cyclic trans-β-Amino Alcohols
    Hu, Qiupeng
    Chen, Jianzhong
    Zhang, Zhenfeng
    Liu, Yangang
    Zhang, Wanbin
    ORGANIC LETTERS, 2016, 18 (06) : 1290 - 1293
  • [36] Highly Chemo- and Enantioselective Rh-Catalyzed Hydrogenation of β-Sulfonyl-α,β-unsaturated Ketones: Access to Chiral γ-Ketosulfones
    Liu, Gang
    Yin, Congcong
    Yang, Xuanliang
    Li, Anqi
    Wang, Minyan
    Zhang, Xumu
    Dong, Xiu-Qin
    ORGANIC LETTERS, 2021, 23 (01) : 19 - 24
  • [37] Practical P-chiral phosphane ligand for Rh-catalyzed asymmetric hydrogenation
    Liu, DA
    Zhang, XM
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (04) : 646 - 649
  • [38] New modular P-chiral ligands for Rh-catalyzed asymmetric hydrogenation
    Bondarev, Oleg G.
    Goddard, Richard
    TETRAHEDRON LETTERS, 2006, 47 (51) : 9013 - 9015
  • [39] Enantioselection mechanism in Rh-catalyzed asymmetric hydrogenation
    I. D. Gridnev
    T. Imamoto
    Russian Chemical Bulletin, 2016, 65 : 1514 - 1534
  • [40] Enantioselection mechanism in Rh-catalyzed asymmetric hydrogenation
    Gridnev, I. D.
    Imamoto, T.
    RUSSIAN CHEMICAL BULLETIN, 2016, 65 (06) : 1514 - 1534