Format

Send to

Choose Destination
Chem Asian J. 2016 Oct 6;11(19):2773-2777. doi: 10.1002/asia.201600445. Epub 2016 Aug 4.

Solvent-Regulated Asymmetric Hydrogenation of Quinoline Derivatives in Oligo(Ethylene Glycol)s through Host-Guest Interactions.

Author information

1
CAS Key Laboratory for Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Science (CAS), and, University of the Chinese Academy of Sciences, Beijing, 100190, P. R. China.
2
CAS Key Laboratory for Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Science (CAS), and, University of the Chinese Academy of Sciences, Beijing, 100190, P. R. China. fanqh@iccas.ac.cn.
3
Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, 300072, P. R. China. fanqh@iccas.ac.cn.

Abstract

The asymmetric hydrogenation of quinolines in oligo(ethylene glycol)s (OEGs) and poly(ethylene glycol)s (PEGs) with chiral cationic ruthenium diamine complexes has been investigated. Interestingly, in liquid PEGs or long-chain OEGs, the Ru catalysts lost their reactivity. Upon the addition of a little MeOH, the hydrogenation of quinoline was switched "ON". Evidence from mass spectrometry and control experiments revealed that encapsulation of the quinolinium salt by PEG or long-chain OEG molecules through supramolecular interactions is possibly the main reason for such a switchable hydrogenation reaction. Moreover, the asymmetric hydrogenation of 2-substituted quinoline derivatives was achieved in triethylene glycol (3-OEG), thereby affording 1,2,3,4-tetrahydroquinolines with excellent reactivities and enantioselectivities (up to 99 % ee). Furthermore, the Ru catalyst could be readily recycled for both pure 3-OEG and biphasic 3-OEG/n-hexane systems without a clear loss of reactivity and enantioselectivity.

KEYWORDS:

asymmetric catalysis; hydrogenation; oligo(ethylene glycol)s; ruthenium; solvent effects

PMID:
27490159
DOI:
10.1002/asia.201600445

Supplemental Content

Full text links

Icon for Wiley
Loading ...
Support Center