Asymmetric Hydrogenation of α,α′-Disubstituted Cycloketones through Dynamic Kinetic Resolution: An Efficient Construction of Chiral Diols with Three Contiguous Stereocenters

被引:79
|
作者
Liu, Chong [1 ,2 ]
Xie, Jian-Hua [1 ,2 ]
Li, Ya-Li [1 ,2 ]
Chen, Ji-Qiang [1 ,2 ]
Zhou, Qi-Lin [1 ,2 ]
机构
[1] Nankai Univ, State Key Lab, Tianjin 300071, Peoples R China
[2] Nankai Univ, Inst Elementoorgan Chem, Tianjin 300071, Peoples R China
基金
中国国家自然科学基金;
关键词
asymmetric hydrogenation; cycloketones; dynamic kinetic resolution; lycorane; ruthenium; BETA-ARYLOXY ALCOHOLS; ENANTIOSELECTIVE SYNTHESIS; CATALYTIC-HYDROGENATION; PHOSPHORUS LIGANDS; RUTHENIUM; ESTERS; KETONES; CYCLIZATION; REDUCTION; COMPLEXES;
D O I
10.1002/anie.201207561
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Chiral diols with three contiguous stereocenters were synthesized by a highly enantioselective ruthenium-catalyzed asymmetric hydrogenation of racemic α,α′-disubstituted cycloketones involving dynamic kinetic resolution. This new catalytic asymmetric method provides a concise route to the alkaloid (+)-γ-lycorane. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:593 / 596
页数:4
相关论文
共 50 条
  • [41] Ru-catalyzed asymmetric hydrogenation of racemic aldehydes via dynamic kinetic resolution: Efficient synthesis of optically active primary alcohols
    Xie, Jian-Hua
    Zhou, Zhang-Tao
    Kong, Wei-Ling
    Zhou, Qi-Lin
    Journal of the American Chemical Society, 2007, 129 (07): : 1868 - 1869
  • [42] Ru-catalyzed asymmetric hydrogenation of racemic aldehydes via dynamic kinetic resolution: Efficient synthesis of optically active primary alcohols
    Xie, Jian-Hua
    Zhou, Zhang-Tao
    Kong, Wei-Ling
    Zhou, Qi-Lin
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (07) : 1868 - +
  • [43] Kinetic Resolution of 2,2-Disubstituted Dihydroquinolines through Chiral Phosphoric Acid-Catalyzed C6-Selective Asymmetric Halogenations
    Zhu, Chaofan
    Liu, Wei
    Zhao, Fei
    Chen, Yunrong
    Tao, Houchao
    He, Yu-Peng
    Yang, Xiaoyu
    ORGANIC LETTERS, 2021, 23 (11) : 4104 - 4108
  • [44] Asymmetric Synthesis of Chiral Acyclic Purine Nucleosides Containing a Hemiaminal Ester Moiety via Three-Component Dynamic Kinetic Resolution
    Xie, Ming-Sheng
    Chen, Yang-Guang
    Wu, Xiao-Xia
    Qu, Gui-Rong
    Guo, Hai-Ming
    ORGANIC LETTERS, 2018, 20 (04) : 1212 - 1215
  • [45] Asymmetric Hydrogenation of Racemic 2-Substituted Indoles via Dynamic Kinetic Resolution: An Easy Access to Chiral Indolines Bearing Vicinal Stereogenic Centers
    Rong, Nianxin
    Zhou, Ao
    Liang, Mingrong
    Wang, Shou-Guo
    Yin, Qin
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2024, 146 (08) : 5081 - 5087
  • [46] Dynamic kinetic resolution in the stereoselective synthesis of 4,5-diaryl cyclic sulfamidates by using chiral rhodium-catalyzed asymmetric transfer hydrogenation
    Han, Juae
    Kang, Soyeong
    Lee, Hyeon-Kyu
    CHEMICAL COMMUNICATIONS, 2011, 47 (13) : 4004 - 4006
  • [47] Synthesis of Axially Chiral Biaryls through Sulfoxide-Directed Asymmetric Mild C-H Activation and Dynamic Kinetic Resolution
    Hazra, Chinmoy Kumar
    Dherbassy, Quentin
    Wencel-Delord, Joanna
    Colobert, Francoise
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (50) : 13871 - 13875
  • [48] Convincing Catalytic Performance of Oxo-Tethered Ruthenium Complexes for Asymmetric Transfer Hydrogenation of Cyclic α-Halogenated Ketones through Dynamic Kinetic Resolution
    Touge, Taichiro
    Nara, Hideki
    Kida, Michio
    Matsumura, Kazuhiko
    Kayaki, Yoshihito
    ORGANIC LETTERS, 2021, 23 (08) : 3070 - 3075
  • [49] Enantioselective and divergent construction of chiral amino alcohols and oxazolidin-2-ones via Ir-f-phamidol-catalyzed dynamic kinetic asymmetric hydrogenation
    Liu, Ruixue
    Ding, Xiaobing
    Lang, Qiwei
    Chen, Gen-Qiang
    Zhang, Xumu
    CHINESE CHEMICAL LETTERS, 2025, 36 (03)
  • [50] Enantioselective and divergent construction of chiral amino alcohols and oxazolidin-2-ones via Ir-f-phamidol-catalyzed dynamic kinetic asymmetric hydrogenation
    Ruixue Liu
    Xiaobing Ding
    Qiwei Lang
    GenQiang Chen
    Xumu Zhang
    Chinese Chemical Letters, 2025, 36 (03) : 322 - 326