A Poly(ethylene glycol)-Supported Multiple Hydrogen Bond Catalyst for the Asymmetric Transfer Hydrogenation of β-Acylamino Nitroolefins

  • Baohua Zhang
  • Lanxiang ShiEmail author


A new poly(ethylene glycol)-supported multiple hydrogen bond catalyst has been prepared and its ability as a promoter in asymmetric transfer hydrogenation of β-acylamino nitroolefins has been studied. The PEG-supported multiple hydrogen bond catalyst exhibits high enantioselective manner (ee up to 95%) and it is easily removable by selective precipitation with diethyl ether and filtration from the reaction mixture, the polymer-bound catalyst has been recycled up to six times no loss of chemical and stereochemical efficiency.

Graphical Abstract


Transfer hydrogenation β-Acylamino nitroolefin PEG-supported hydrogen bond catalyst β-Acylamino nitroalkane 



This study was supported by the Chna’s Hebei Province Science and Technology Support (No. 18271404D).

Compliance with Ethical Standards

Conflict of interest

The authors declare that they have no conflict of interest.


  1. 1.
    Blaser HU, Malan C, Pugin B et al (2003) Selective hydrogenation for fine chemicals: recent trends and new developments. Adv Synth Catal 345:103. CrossRefGoogle Scholar
  2. 2.
    Carpentier JF, Bette V (2002) Chemo- and enantioselective hydrosilylation of carbonyl and imino groups. An emphasis on non-traditional catalyst systems. Curr Org Chem 6:913. CrossRefGoogle Scholar
  3. 3.
    Zhou M, Dong DJ, Zhu BL et al (2013) Rhodium-catalyzed enantioselective hydrogenation of β-acylamino nitroolefins: a new approach to chiral β-amino nitroalkanes. Org Lett 15:5524. CrossRefGoogle Scholar
  4. 4.
    Xie JH, Zhu SF, Zhou QL (2011) Transition metal-catalyzed enantioselective hydrogenation of enamines and imines. Chem Rev 111:1713. CrossRefGoogle Scholar
  5. 5.
    Schneider JF, Lauber MB, Muhr VJ et al (2011) Readily available hydrogen bond catalysts for the asymmetric transfer hydrogenation of nitroolefins. Org Biomol Chem 9:4323. CrossRefGoogle Scholar
  6. 6.
    Liu XW, Yan Y, Wang YQ et al (2012) Highly enantioselective reduction of β-amino nitroolefins with a simple N-sulfinyl urea as bifunctional catalyst. Chem Eur J 18:9204. CrossRefGoogle Scholar
  7. 7.
    Artinelli E, Vicini AC, Mancinell M et al (2015) Catalytic highly enantioselective transfer hydrogenation of β-trifluoromethyl nitroalkenes. An easy and general entry to optically active β-trifluoromethyl amines. Chem Commun 51:658. CrossRefGoogle Scholar
  8. 8.
    Reger TS, Janda KD (2000) Polymer-supported (salen)Mn catalysts for asymmetric epoxidation: a comparison between soluble and insoluble matrices. J Am Chem Soc 122:6929. CrossRefGoogle Scholar
  9. 9.
    Wentworth P, Janda KD (1999) Liquid-phase chemistry: recent advances in soluble polymer-supported catalysts, reagents and synthesis. Chem Commun. Google Scholar
  10. 10.
    Long J, Gao WC, Guan YQ et al (2018) Nickel-catalyzed highly enantioselective hydrogenation of β-acetylamino vinylsulfones: access to chiral β-amido sulfones. Org Lett 20:5914. CrossRefGoogle Scholar
  11. 11.
    Wang BT, Zhang SG, Zhen B et al (2017) Synthesis of chloro-termination polyethylene glycol via reaction of polyethylene glycol and thionyl chloride. J Chem Eng Chin Univ 31:1389. Google Scholar

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  1. 1.College of Chemical EngineeringShijiazhuang UniversityShijiazhuangChina

Personalised recommendations