Journal of the Iranian Chemical Society

, Volume 5, Issue 3, pp 384–393

Sulfamic acid catalyzed ring opening of epoxides with amines under solvent-free conditions

Article

DOI: 10.1007/BF03245992

Cite this article as:
Hosseini-Sarvari, M. & Sharghi, H. JICS (2008) 5: 384. doi:10.1007/BF03245992

Abstract

Sulfamic acid (SA) catalyses the nucleophilic opening of epoxide rings by amines leading to the efficient synthesis of ß-amino alcohols. The reaction works well with aromatic and aliphatic amines in short reaction times and in the absence of solvent. Exclusive trans stereoselectivity is observed for the ring opening of cyclohexene oxide. This method exhibits excellent regioselectivity for preferential nucleophilic attack at the less hindered position during the reaction with unsymmetrical epoxides.

Keywords

Sulfamic acidEpoxideAminesß-Amino alcohols

Copyright information

© Iranian Chemical Society 2008

Authors and Affiliations

  1. 1.Department of Chemistry, College of ScienceShiraz UniversityShirazIran