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] α,β-Unsaturated imines via Ru-catalyzed coupling of allylic alcohols and amines
    Rigoli, Jared W.
    Moyer, Sara A.
    Pearce, Simon D.
    Schomaker, Jennifer M.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (09) : 1746 - 1749
  • [22] Synthesis of chiral chromanols via a RuPHOX- Ru catalyzed asymmetric hydrogenation of chromones
    Ma, Yujie
    Li, Jing
    Ye, Jianxun
    Liu, Delong
    Zhang, Wanbin
    CHEMICAL COMMUNICATIONS, 2018, 54 (96) : 13571 - 13574
  • [23] Synthesis of Chiral Diaryl Methanols via RuPHOX-Ru Catalyzed Asymmetric Hydrogenation
    Zhou, Jiayu
    Ye, Jianxun
    Zhang, Yang
    Li, Zhaodi
    Li, Jingjing
    Liu, Delong
    Zhang, Wanbin
    ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (08) : 1275 - 1286
  • [24] Atropos but achiral tris(phosphanyl)biphenyl ligands for RU-catalyzed asymmetric hydrogenation
    Aikawa, K
    Mikami, K
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (44) : 5455 - 5458
  • [25] Ru-catalyzed asymmetric hydrogenation of δ-keto Weinreb amides: enantioselective synthesis of (+)-Centrolobine
    Zhao, Mengmeng
    Lu, Bin
    Ding, Guangni
    Ren, Kai
    Xie, Xiaomin
    Zhang, Zhaoguo
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (09) : 2723 - 2730
  • [26] Convenient synthesis of enamides via Ru-catalyzed addition of amides to alkynes.
    Goossen, LJ
    Rauhaus, JE
    Deng, GJ
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 229 : U584 - U584
  • [27] Highly effective chiral dipyridylphosphine ligands: Synthesis, structural determination, and applications in the Ru-catalyzed asymmetric hydrogenation reactions
    Pai, CC
    Lin, CW
    Lin, CC
    Chen, CC
    Chan, ASC
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (46) : 11513 - 11514
  • [28] A Selective Ru-Catalyzed Semireduction of Alkynes to Z Olefins under Transfer-Hydrogenation Conditions
    Belger, Christian
    Neisius, N. Matthias
    Plietker, Bernd
    CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (40) : 12214 - 12220
  • [29] Synthesis and structural characterization of a highly effective chiral dipyridylphosphine ligand and its application in the Ru-catalyzed asymmetric hydrogenation of β-ketoesters
    Wu, J
    Chen, H
    Zhou, ZY
    Yeung, CH
    Chan, ASC
    SYNLETT, 2001, : 1050 - 1054
  • [30] Chiral 1,2,3,4-tetrahydroquinolinyl-oxazoline ligands for Ru-catalyzed asymmetric transfer hydrogenation of ketones
    Zhou, YB
    Tang, FY
    Xu, HD
    Wu, XY
    Ma, JA
    Zhou, QL
    TETRAHEDRON-ASYMMETRY, 2002, 13 (05) : 469 - 473