Transformation of Alkynes into Chiral Alcohols via TfOH-Catalyzed Hydration and Ru-Catalyzed Tandem Asymmetric Hydrogenation

被引:34
|
作者
Liu, Sensheng [1 ]
Liu, Huan [1 ]
Zhou, Haifeng [1 ,2 ]
Liu, Qixing [1 ]
Lv, Jinliang [2 ]
机构
[1] China Three Gorges Univ, Coll Biol & Pharmaceut Sci, Res Ctr Green Pharmaceut Technol & Proc, Hubei Key Lab Nat Prod Res & Dev, Yichang 443002, Peoples R China
[2] Yichang Humanwell Pharmaceut Co Ltd, Yichang 443005, Peoples R China
基金
中国国家自然科学基金;
关键词
HIGHLY ENANTIOSELECTIVE HYDROGENATION; ANTI-MARKOVNIKOV HYDRATION; TERMINAL ALKYNES; REGIOSELECTIVE HYDRATION; AMBIENT-TEMPERATURE; REDUCTIVE HYDRATION; IONIC LIQUID; COMPLEXES; KETONES; WATER;
D O I
10.1021/acs.orglett.8b00034
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel full atom-economic process for the transformation of alkynes into chiral alcohols by TfOH-catalyzed hydration coupled with Ru-catalyzed tandem asymmetric hydrogenation in TFE under simple conditions has been developed. A range of chiral alcohols was obtained with broad functional group tolerance, good yields, and excellent stereoselectivities.
引用
收藏
页码:1110 / 1113
页数:4
相关论文
共 50 条
  • [21] Enantioselective Synthesis of 1-Aryl-Substituted Tetrahydroisoquinolines Through Ru-Catalyzed Asymmetric Transfer Hydrogenation
    Perez, Marc
    Wu, Zi
    Scalone, Michelangelo
    Ayad, Tahar
    Ratovelomanana-Vidal, Virginie
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (29) : 6503 - 6514
  • [22] Ruthenium-Catalyzed Asymmetric Hydrogenation of β-Ketoenamines: An Efficient Approach to Chiral γ-Amino Alcohols
    Geng, Huiling
    Zhang, Xiaowei
    Chang, Mingxin
    Zhou, Le
    Wu, Wenjun
    Zhang, Xumu
    ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (16) : 3039 - 3043
  • [23] Efficient asymmetric hydrogenation of quinolines in neat water catalyzed by chiral cationic Ru-diamine complexes
    Yang, Zhusheng
    Chen, Fei
    He, Yan-Mei
    Yang, Nianfa
    Fan, Qing-Hua
    CATALYSIS SCIENCE & TECHNOLOGY, 2014, 4 (09) : 2887 - 2890
  • [24] Building Molecular Complexity via Tandem Ru-catalyzed Isomerization/C-H Activation
    Bartoszewicz, Agnieszka
    Martin-Matute, Belen
    ORGANIC LETTERS, 2009, 11 (08) : 1749 - 1752
  • [25] Kinetic resolution of azaflavanones via a RuPHOX-Ru catalyzed asymmetric hydrogenation
    Zhu, Yue
    Zhou, Jiayu
    Li, Jing
    Xu, Kai
    Ye, Jianxun
    Lu, Yufei
    Liu, Delong
    Zhang, Wanbin
    ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (23) : 6609 - 6615
  • [26] Chiral Gold Phosphate Catalyzed Tandem Hydroamination/Asymmetric Transfer Hydrogenation Enables Access to Chiral Tetrahydroquinolines
    Du, Yu-Liu
    Hu, Yue
    Zhu, Yi-Fan
    Tu, Xi-Feng
    Han, Zhi-Yong
    Gong, Liu-Zhu
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (09): : 4754 - 4759
  • [27] Highly Enantioselective One-Pot Synthesis of Chiral β-Heterosubstituted Alcohols via Ruthenium-Prolinamide-Catalyzed Asymmetric Transfer Hydrogenation
    Vyas, Vijyesh K.
    Srivastava, Prasenjit
    Bhatt, Prachi
    Shende, Vaishali
    Ghosh, Pushpito
    Bhanage, Bhalchandra M.
    ACS OMEGA, 2018, 3 (10): : 12737 - 12745
  • [28] Ru-Catalyzed asymmetric transfer hydrogenation of substituted dibenzo[b,f][1,4]oxazepines in water
    More, Ganesh V.
    Bhanage, Bhalchandra M.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (25) : 5263 - 5267
  • [29] Catalyzed or non-catalyzed: chemoselectivity of Ru-catalyzed acceptorless dehydrogenative coupling of alcohols and amines via metal-ligand bond cooperation and (de) aromatization
    Shu, Siwei
    Huang, Meijie
    Jiang, Jingxing
    Qu, Ling-Bo
    Liu, Yan
    Ke, Zhuofeng
    CATALYSIS SCIENCE & TECHNOLOGY, 2019, 9 (09) : 2305 - 2314
  • [30] Rh-Catalyzed Asymmetric Hydrogenation of β-Branched Enol Esters for the Synthesis of β-Chiral Primary Alcohols
    Liu, Chong
    Yuan, Jing
    Zhang, Jian
    Wang, Zhihui
    Zhang, Zhenfeng
    Zhang, Wanbin
    ORGANIC LETTERS, 2018, 20 (01) : 108 - 111