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: bieberlothar
hotmail.com
L. W. Bieber, M. C. F. de Araujo, Molecules, 2002, 7, 902-906.
Abstract
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
