Display options
Cite
Seibel ZM, Bandar JS, Lambert TH. Enantioenriched α-substituted glutamates/pyroglutamates via enantioselective cyclopropenimine-catalyzed Michael addition of amino ester imines. Beilstein J Org Chem. 2021;17:2077-2084doi: 10.3762/bjoc.17.134.
Seibel, Z. M., Bandar, J. S., & Lambert, T. H. (2021). Enantioenriched α-substituted glutamates/pyroglutamates via enantioselective cyclopropenimine-catalyzed Michael addition of amino ester imines. Beilstein journal of organic chemistry, 172077-2084. https://doi.org/10.3762/bjoc.17.134
Seibel, Zara M, et al. "Enantioenriched α-substituted glutamates/pyroglutamates via enantioselective cyclopropenimine-catalyzed Michael addition of amino ester imines." Beilstein journal of organic chemistry vol. 17 (2021): 2077-2084. doi: https://doi.org/10.3762/bjoc.17.134
Seibel ZM, Bandar JS, Lambert TH. Enantioenriched α-substituted glutamates/pyroglutamates via enantioselective cyclopropenimine-catalyzed Michael addition of amino ester imines. Beilstein J Org Chem. 2021 Aug 17;17:2077-2084. doi: 10.3762/bjoc.17.134. eCollection 2021. PMID: 34476014; PMCID: PMC8381810.
Copy Download .nbib Format: NLM
Share it on

Beilstein J Org Chem. 2021 Aug 17;17:2077-2084. doi: 10.3762/bjoc.17.134. eCollection 2021.

Enantioenriched α-substituted glutamates/pyroglutamates via enantioselective cyclopropenimine-catalyzed Michael addition of amino ester imines.

Beilstein journal of organic chemistry

Zara M Seibel, Jeffrey S Bandar, Tristan H Lambert

Affiliations

  1. Department of Chemistry, Columbia University, New York, New York 10027, USA.
  2. Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York 14853, USA.

PMID: 34476014 PMCID: PMC8381810 DOI: 10.3762/bjoc.17.134

Abstract

A procedure for the enantioselective synthesis of α-substituted glutamates and pyroglutamates via a cyclopropenimine-catalyzed Michael addition of amino ester imines is described. Enantioselectivities of up to 94% have been achieved, and a variety of functional groups were found to be compatible. The impact of the catalyst structure and imine substitution is discussed. Compared to other methods, this protocol allows for a broader and more enantioselective access to pyroglutamate derivatives.

Copyright © 2021, Seibel et al.

Keywords: Brønsted base; Michael addition; cyclopropenimine; enantioselective catalysis; pyroglutamate

References

  1. Org Lett. 2007 Jun 7;9(12):2289-92 - PubMed
  2. Org Lett. 2011 Oct 21;13(20):5600-3 - PubMed
  3. J Am Chem Soc. 2012 Mar 28;134(12):5552-5 - PubMed
  4. Angew Chem Int Ed Engl. 2008;47(25):4687-90 - PubMed
  5. Chem Sci. 2015 Feb 1;6(2):1537-1547 - PubMed
  6. Org Lett. 2008 Apr 3;10(7):1461-3 - PubMed
  7. Angew Chem Int Ed Engl. 2010 Dec 3;49(49):9346-67 - PubMed
  8. Angew Chem Int Ed Engl. 2007;46(35):6703-5 - PubMed
  9. Science. 1995 May 5;268(5211):726-31 - PubMed
  10. J Am Chem Soc. 2005 Jun 15;127(23):8298-9 - PubMed
  11. J Antibiot (Tokyo). 1991 Jan;44(1):113-6 - PubMed
  12. Org Lett. 2016 May 6;18(9):1996-9 - PubMed
  13. J Org Chem. 2004 Oct 29;69(22):7558-64 - PubMed
  14. Chem Commun (Camb). 2004 May 21;(10):1230-1 - PubMed
  15. Org Lett. 2001 May 31;3(11):1761-3 - PubMed
  16. J Org Chem. 2004 Feb 20;69(4):1180-5 - PubMed
  17. J Org Chem. 2001 Nov 2;66(22):7555-9 - PubMed
  18. J Am Chem Soc. 2004 May 26;126(20):6230-1 - PubMed
  19. Org Lett. 2000 Jul 13;2(14):1987-90 - PubMed
  20. Chem Commun (Camb). 2011 Mar 21;47(11):3219-21 - PubMed
  21. Org Lett. 2007 May 24;9(11):2143-6 - PubMed
  22. Angew Chem Int Ed Engl. 2003 Jan 20;42(3):355-7 - PubMed
  23. J Am Chem Soc. 2014 Jul 30;136(30):10700-7 - PubMed
  24. Chem Asian J. 2007 Jan 8;2(1):20-38 - PubMed
  25. Org Lett. 2009 May 7;11(9):2023-5 - PubMed

Publication Types