Molecules 2002, 7(12), 902-906; doi:10.3390/71200902
Article

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

Lothar W. Bieber* email and Maria C. F. De Araújo
Departamento de Química Fundamental, Universidade Federal de Pernambuco, 50607-901 Recife – PE, Brazil
* Author to whom correspondence should be addressed.
Received: 3 November 2002; in revised form: 2 December 2002 / Accepted: 2 December 2002 / Published: 31 December 2002
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Abstract: 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.
Keywords: Amino alcohols; bis-tosylation; inorganic bases; 1; 3-elimination; aqueous solvent

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MDPI and ACS Style

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.

AMA Style

Bieber LW, De Araújo MCF. Short and Efficient Synthesis of Optically Active N-Tosyl Aziridines from 2-Amino Alcohols. Molecules. 2002; 7(12):902-906.

Chicago/Turabian Style

Bieber, Lothar W.; De Araújo, Maria C.F. 2002. "Short and Efficient Synthesis of Optically Active N-Tosyl Aziridines from 2-Amino Alcohols." Molecules 7, no. 12: 902-906.

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