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European J Org Chem. 2015 Apr;2015(11):2374-2381. doi: 10.1002/ejoc.201403555. Epub 2015 Feb 20.

Coordinating Chiral Ionic Liquids: Design, Synthesis, and Application in Asymmetric Transfer Hydrogenation under Aqueous Conditions.

European journal of organic chemistry

Maria Vasiloiu, Peter Gaertner, Ronald Zirbs, Katharina Bica

Affiliations

  1. Institute of Applied Synthetic Chemistry, Vienna University of Technology Getreidemarkt 9/163, 1060 Vienna, Austria E-mail: [email protected] http://www.ias.tuwien.ac.at/home/
  2. Laboratory for Bioinspired Materials, Department of NanoBiotechnology, BOKU - University of Natural Resources and Life Sciences Vienna Muthgasse 11, 1190 Vienna, Austria.

PMID: 26279638 PMCID: PMC4529664 DOI: 10.1002/ejoc.201403555

Abstract

Hydrophilic coordinating chiral ionic liquids with an amino alcohol substructure were developed and efficiently applied to the asymmetric reduction of ketones. Their careful design and adaptability to the desired reaction conditions allow for these chiral ionic liquids to be used as the sole source of chirality in a ruthenium-catalyzed transfer hydrogenation reaction of aromatic ketones. When used in this reaction system, these chiral ionic liquids afforded excellent yields and high enantioselectivities.

Keywords: Asymmetric catalysis; Hydrogenation; Ionic liquids; Ketones; Ruthenium; Self-assembly

References

  1. Chirality. 2005 May 15;17(5):281-92 - PubMed
  2. Org Biomol Chem. 2013 Dec 14;11(46):8092-102 - PubMed
  3. Angew Chem Int Ed Engl. 2005 Nov 11;44(44):7174-99 - PubMed
  4. Chem Asian J. 2009 Aug 3;4(8):1184-95 - PubMed
  5. J Org Chem. 2004 Jul 23;69(15):4885-90 - PubMed
  6. Chem Commun (Camb). 2007 Jun 28;(24):2449-66 - PubMed
  7. J Org Chem. 2007 Nov 23;72(24):9350-2 - PubMed
  8. Org Lett. 2009 Oct 1;11(19):4286-8 - PubMed
  9. Chem Rev. 2007 Dec;107(12):5606-55 - PubMed
  10. Chem Commun (Camb). 2001 Oct 21;(20):2064-5 - PubMed
  11. Angew Chem Int Ed Engl. 2007;46(8):1293-5 - PubMed
  12. Chemistry. 2010 Jan 18;16(3):836-47 - PubMed
  13. J Org Chem. 2000 May 19;65(10):3116-22 - PubMed
  14. Chem Commun (Camb). 2012 Jan 28;48(8):1105-7 - PubMed
  15. Chemistry. 2014 Oct 20;20(43):13889-93 - PubMed
  16. Chem Commun (Camb). 2012 May 21;48(41):5013-5 - PubMed
  17. Angew Chem Int Ed Engl. 2006 May 26;45(22):3689-92 - PubMed
  18. Org Lett. 2003 Oct 30;5(22):4227-30 - PubMed
  19. J Am Chem Soc. 2012 Nov 14;134(45):18522-5 - PubMed
  20. Phys Chem Chem Phys. 2014 Apr 7;16(13):5893-906 - PubMed

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