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Short and Efficient Synthesis of Optically Active N-Tosyl Aziridines from 2-Amino Alcohols

Lothar W. Bieber* and Maria C. F. de Araújo

*Departamento de Química Fundamental, Universidade Federal de Pernambuco, 50607-901 Recife - PE, Brazil, Email:

L. W. Bieber, M. C. F. de Araujo, Molecules, 2002, 7, 902-906.


Two alternative and complementary one-pot procedures for the direct transformation of 2-amino alcohols to N-tosyl aziridines are presented. Less hindered aziridines can be obtained in high yields by tosylation and in situ cyclization effected by potassium hydroxide in water/dichloromethane. Higher substituted amino alcohols give better yields using potassium carbonate in acetonitrile.

Reaction Pathway

Key Words

Amino alcohols, Tosylation, Inorganic bases, 1,3-elimination, aqueous solvent, Wenker Synthesis, Aziridines

ID: J51-Y2002-X