Display options
Cite
Napolitano T, Cheng SY, Nielsen B, et al. Acetone promoted 1,4-migration of an alkoxycarbonyl group on a syn-1,2-diamine. Tetrahedron Lett. 2017;58(7):597-601doi: 10.1016/j.tetlet.2016.12.047.
Napolitano, T., Cheng, S. Y., Nielsen, B., Choi, C., Aguilar, W., Paz, M. M., Sapse, A. M., & Champeil, E. (2017). Acetone promoted 1,4-migration of an alkoxycarbonyl group on a syn-1,2-diamine. Tetrahedron letters, 58(7), 597-601. https://doi.org/10.1016/j.tetlet.2016.12.047
Napolitano, Tanya, et al. "Acetone promoted 1,4-migration of an alkoxycarbonyl group on a syn-1,2-diamine." Tetrahedron letters vol. 58,7 (2017): 597-601. doi: https://doi.org/10.1016/j.tetlet.2016.12.047
Napolitano T, Cheng SY, Nielsen B, Choi C, Aguilar W, Paz MM, Sapse AM, Champeil E. Acetone promoted 1,4-migration of an alkoxycarbonyl group on a syn-1,2-diamine. Tetrahedron Lett. 2017 Feb 15;58(7):597-601. doi: 10.1016/j.tetlet.2016.12.047. Epub 2017 Jan 03. PMID: 28943668; PMCID: PMC5604470.
Copy Download .nbib Format: NLM
Share it on

Tetrahedron Lett. 2017 Feb 15;58(7):597-601. doi: 10.1016/j.tetlet.2016.12.047. Epub 2017 Jan 03.

Acetone promoted 1,4-migration of an alkoxycarbonyl group on a syn-1,2-diamine.

Tetrahedron letters

Tanya Napolitano, Shu-Yuan Cheng, Brooke Nielsen, Christopher Choi, William Aguilar, Manuel M Paz, Anne-Marie Sapse, Elise Champeil

Affiliations

  1. John Jay College of Criminal Justice, New York, 524 west 59 Street, New York, NY, 10019, USA.
  2. Ph.D. Program in Biochemistry, The Graduate Center of the City University of New York, New York, NY 10016, USA.
  3. Departamento de Química Orgánica, Facultade de Química, Universidade de Santiago de Compostela, 15782 Santiago de Compostela, Spain.
  4. Ph.D. Program in Chemistry, The Graduate Center of the City University of New York, New York, NY 10016, USA.

PMID: 28943668 PMCID: PMC5604470 DOI: 10.1016/j.tetlet.2016.12.047

Abstract

A 2-protected cis-amino mitosene undergoes an irreversible acetone promoted isomerization and converts to the 1-isomer. Kinetic studies and DFT calculations of the reaction are reported. An organocatalytic mechanism is proposed, involving a covalent intermediate formed by reaction of the mitosene and acetone.

Keywords: Acetone; Alkoxycarbonyl migration; Mitosene; Organocatalytic mechanism

References

  1. Bioorg Chem. 2016 Apr;65:90-9 - PubMed
  2. Org Lett. 2006 Dec 21;8(26):6047-9 - PubMed
  3. Org Lett. 2010 Sep 17;12(18):4030-3 - PubMed
  4. Bioorg Med Chem Lett. 2010 Jan 1;20(1):31-4 - PubMed
  5. Chem Res Toxicol. 2010 Jul 19;23 (7):1151-62 - PubMed
  6. Int J Oncol. 2016 Nov;49(5):1815-1824 - PubMed
  7. Bioorg Med Chem Lett. 2012 Dec 1;22(23):7198-200 - PubMed
  8. J Am Chem Soc. 2008 Jul 23;130(29):9556-65 - PubMed
  9. Chem Res Toxicol. 2002 Nov;15(11):1398-406 - PubMed
  10. Chem Res Toxicol. 2008 Dec;21(12):2370-8 - PubMed
  11. Org Lett. 2013 Feb 15;15(4):836-9 - PubMed
  12. Biochemistry. 1990 Mar 27;29(12):2999-3006 - PubMed
  13. J Med Chem. 1985 Jul;28(7):963-7 - PubMed
  14. Chem Res Toxicol. 2012 Jul 16;25(7):1502-11 - PubMed
  15. J Antibiot (Tokyo). 1956 Jul;9(4):141-6 - PubMed
  16. Nucleic Acids Res. 2010 Nov;38(20):6976-84 - PubMed
  17. Org Lett. 2009 Feb 19;11(4):791-4 - PubMed
  18. J Med Chem. 1975 Mar;18(3):307-11 - PubMed

Publication Types

Grant support