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
  • [31] Ir- and Ru-catalyzed sequential reactions:: Asymmetric α-alkylative reduction of ketones with alcohols
    Onodera, Gen
    Nishibayashi, Yoshiaki
    Uemura, Sakae
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (23) : 3819 - 3822
  • [32] A new chiral dipyridylphosphine ligand Xyl-P-Phos and its application in the Ru-catalyzed asymmetric hydrogenation of β-ketoesters
    Wu, J
    Chen, H
    Kwok, WH
    Lam, KH
    Zhou, ZY
    Yeung, CH
    Chan, ASC
    TETRAHEDRON LETTERS, 2002, 43 (08) : 1539 - 1543
  • [33] Synthesis of chiral γ-lactones via a RuPHOX-Ru catalyzed asymmetric hydrogenation of aroylacrylic acids
    Lu, Yufei
    Li, Jing
    Zhu, Yue
    Shen, Jiefeng
    Liu, Delong
    Zhang, Wanbin
    TETRAHEDRON, 2019, 75 (26) : 3643 - 3649
  • [34] Ru-catalyzed asymmetric transfer hydrogenation of racemic /3-keto γ-lactams via dynamic kinetic resolution
    Malekar, Pushpa, V
    More, Ganesh, V
    Ramana, Chepuri, V
    TETRAHEDRON, 2024, 167
  • [35] Ru-Catalyzed Asymmetric Addition of Arylboronic Acids to Aliphatic Aldehydes via P-Chiral Monophosphorous Ligands
    Miao, Rui
    Xia, Yanping
    Wei, Yifei
    Ouyang, Lu
    Luo, Renshi
    MOLECULES, 2022, 27 (12):
  • [36] t-Bu-QuinoxP* ligand: Applications in asymmetric pd-catalyzed allylic substitution and Ru-catalyzed hydrogenation
    Imamoto, Tsuneo
    Nishimura, Miwako
    Koide, Aya
    Yoshida, Kazuhiro
    JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (19): : 7413 - 7416
  • [37] Self-assembled bidentate ligands for Ru-catalyzed anti-Markovnikov hydration of terminal alkynes
    Chevallier, F
    Breit, B
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (10) : 1599 - 1602
  • [38] New chiral amino alcohol ligands derived from 1-phenylethylamine for efficient Ru-catalyzed asymmetric transfer hydrogenation
    Han, Mei-Ling
    Hu, Xiang-Ping
    Huang, Jia-Di
    Chen, Li-Gong
    Zheng, Zhuo
    TETRAHEDRON-ASYMMETRY, 2011, 22 (02) : 222 - 225
  • [39] New chiral phosphinite ligands with C2-symmetric axis and their possible applications in Ru-catalyzed asymmetric transfer hydrogenation
    Aydemir, Murat
    Meric, Nermin
    Baysal, Akin
    Kayan, Cezmi
    Togrul, Mahmut
    Gumgum, Bahattin
    APPLIED ORGANOMETALLIC CHEMISTRY, 2010, 24 (03) : 215 - 221
  • [40] Primary trifluoroborate-iminiums enable facile access to chiral α-aminoboronic acids via Ru-catalyzed asymmetric hydrogenation and simple hydrolysis of the trifluoroborate moiety
    Sterman, Andrej
    Sosic, Izidor
    Casar, Zdenko
    CHEMICAL SCIENCE, 2022, 13 (10) : 2946 - 2953