Display options
Share it on

Org Biomol Chem. 2017 Feb 21;15(7):1718-1724. doi: 10.1039/c6ob02801b. Epub 2017 Jan 31.

Chiral GAP catalysts of phosphonylated imidazolidinones and their applications in asymmetric Diels-Alder and Friedel-Crafts reactions.

Organic & biomolecular chemistry

Shuo Qiao, Junming Mo, Cody B Wilcox, Bo Jiang, Guigen Li

Affiliations

  1. Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas 79409-1061, USA. [email protected].

PMID: 28139798 PMCID: PMC5323037 DOI: 10.1039/c6ob02801b

Abstract

The design and synthesis of recyclable imidazolidinone catalysts using GAP chemistry/technique was described. Their applications in asymmetric Diels-Alder and Friedel-Crafts reactions with α,β-unsaturated aldehydes resulted in excellent yields and higher enantioselectivities than previous processes. As recyclable small molecular catalysts, phosphonylated imidazolidinones can be recovered and reused for up to three runs without costing significant decrease in catalytic activity.

References

  1. Beilstein J Org Chem. 2015 May 12;11:730-8 - PubMed
  2. Angew Chem Int Ed Engl. 2008;47(37):6960-8 - PubMed
  3. Chirality. 2005 May 15;17(5):281-92 - PubMed
  4. Chem Asian J. 2009 Aug 3;4(8):1184-95 - PubMed
  5. RSC Adv. 2013 Jan 1;3(36):15820-15826 - PubMed
  6. Acc Chem Res. 2006 Dec;39(12):897-908 - PubMed
  7. Chem Rev. 2003 Sep;103(9):3401-29 - PubMed
  8. Org Biomol Chem. 2015 Feb 14;13(6):1600-17 - PubMed
  9. Chem Commun (Camb). 2012 Jun 14;48(47):5856-8 - PubMed
  10. Org Lett. 2016 Apr 1;18(7):1602-5 - PubMed
  11. Synlett. 2008 Apr 1;2008(7):999-1004 - PubMed
  12. J Org Chem. 2011 Apr 15;76(8):2792-7 - PubMed
  13. Chem Rev. 2003 Aug;103(8):2985-3012 - PubMed
  14. Org Lett. 2012 Jul 20;14(14):3668-71 - PubMed
  15. Chem Soc Rev. 2009 Aug;38(8):2178-89 - PubMed
  16. Angew Chem Int Ed Engl. 2001 Feb 2;40(3):529-532 - PubMed
  17. J Am Chem Soc. 2001 May 9;123(18):4370-1 - PubMed
  18. Chemistry. 2016 Dec 12;22(50):18254-18258 - PubMed
  19. Science. 2002 Dec 6;298(5600):1904-5 - PubMed
  20. Beilstein J Org Chem. 2014 Mar 13;10:653-9 - PubMed
  21. Chemistry. 2010 Oct 18;16(39):11963-8 - PubMed
  22. Chem Commun (Camb). 2006 Mar 14;(10):1049-63 - PubMed
  23. Science. 2003 Mar 14;299(5613):1702-6 - PubMed
  24. Bioorg Med Chem. 2011 Sep 15;19(18):5352-60 - PubMed
  25. Chem Rev. 2007 Dec;107(12):5416-70 - PubMed
  26. Chem Rev. 2009 Feb;109(2):418-514 - PubMed
  27. Angew Chem Int Ed Engl. 2004 Oct 4;43(39):5138-75 - PubMed

Publication Types

Grant support