Ring Opening of 6-Azabicyclo[3.1.0]hex-3-en-2-ols in Water under Mild Conditions

Joao R. Vale, Filipa Siopa, Paula Cristina de Sério Branco, Carlos A M Afonso

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

The ring-opening reaction of -hydroxycyclopenteno-aziridines (6-azabicyclo[3.1.0]hex-3-en-2-ols) was investigated in water and under physiological conditions (pH = 7.4) at 37 degrees C by using a range of carbon-, oxygen-, nitrogen-, and sulfur-containing nucleophiles such as azides, anilines, and thiols (aryl and alkyl thiols as well as cysteine and its derivatives), which provided the products in moderate to high isolated yields. The reactivity was also demonstrated in the bioconjugation of -hydroxycyclopenteno-aziridine with the peptide hormone salmon calcitonin (sCT).

Original languageEnglish
Pages (from-to)2048-2053
Number of pages6
JournalEuropean Journal of Organic Chemistry
Volume11
DOIs
Publication statusPublished - Apr 2016

Keywords

  • Water chemistry
  • Nucleophilic substitution
  • Chemoselectivity
  • Fused-ring systems
  • Carbocycles

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