Asymmetric one-pot synthesis of cyclopropanes


  • Naoufel Ben Hamadi Al Imam Mohammad Ibn Saud Islamic University (IMSIU), College of Sciences, Department of Chemistry, 11623 Riyadh
  • Ahlem Guesmi Al Imam Mohammad Ibn Saud Islamic University (IMSIU), College of Sciences, Department of Chemistry, 11623 Riyadh
  • Wided Nouira Laboratory of Interfaces and Advanced Materials, University of Monastir, Avenue of Environment, 5019 Monastir



1, 3-dipolar cycloaddition, aromatic nitrile oxides, propargyl O-glycoside, isoxazole.


Cycloaddition of the diazoalkanes to electron-deficient olefins (in situ) affords polysubstituted cyclopropanes in high yields (up to 85%). Deprotection of the ketal protecting group provided water-soluble cyclopropane-bearing carbohydrate in good yields. Antimicrobial activity screening of the synthesized compounds 8 and 9, utilizing a variety of Gram-positive (Staphylococcus aureus and Enterococcus fecalis), Gram-negative bacteria (Escherichia coli and Klebsiella pneumoniae) and yeast (Candida albicans), exhibited that all the prepared analogues acquire promising activities against both Gram-positive and Gram-negative bacteria especially compounds 9b and 9c (antimicrobial active agents against Gram-negative bacteria).

Author Biography

Ahlem Guesmi, Al Imam Mohammad Ibn Saud Islamic University (IMSIU), College of Sciences, Department of Chemistry, 11623 Riyadh



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How to Cite

Ben Hamadi, N., Guesmi, A., & Nouira, W. (2016). Asymmetric one-pot synthesis of cyclopropanes. Macedonian Journal of Chemistry and Chemical Engineering, 35(1), 45–52.



Organic Chemistry