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

Departamento de Química Fundamental, Universidade Federal de Pernambuco, 50607-901 Recife – PE, Brazil
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Molecules 2002, 7(12), 902-906; https://doi.org/10.3390/71200902
Received: 3 November 2002 / Revised: 2 December 2002 / Accepted: 2 December 2002 / Published: 31 December 2002
Two alternative and complementary one-pot procedures for the direct transformation of 2-amino alcohols to N-tosyl aziridines are presented. The unsubstituted parent compound and its less hindered homologues can be obtained in high yields by tosylation and in situ cyclisation effected by potassium hydroxide in water/dichloromethane. Higher substituted amino alcohols give better yields using potassium carbonate in acetonitrile. Both procedures use simple inorganic bases and produce only inorganic salts as byproducts. View Full-Text
Keywords: Amino alcohols; bis-tosylation; inorganic bases; 1; 3-elimination; aqueous solvent Amino alcohols; bis-tosylation; inorganic bases; 1; 3-elimination; aqueous solvent
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Bieber, L.W.; De Araújo, M.C.F. Short and Efficient Synthesis of Optically Active N-Tosyl Aziridines from 2-Amino Alcohols. Molecules 2002, 7, 902-906.

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