Short and Efficient Synthesis of Optically Active N-Tosyl Aziridines from 2-Amino Alcohols 英文参考文献.docVIP

Molecules 2002, 7, 902-906 molecules ISSN 1420-3049 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 *Author to whom correspondence should be addressed; e-mail: bieberlothar@ Received: 3 November 2002; in revised form: 2 December 2002 / Accepted 2 December 2002 / Published 31 December 2002 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. Introduction Aziridines are interesting synthetic building blocks for the construction of complex nitrogen containing compounds. When activated by a N-tosyl group, they are especially reactive towards nucleophilic ring opening and provide an easy access to a wide variety of alkaloid structures [1]. Although several methods have been reported for the direct asymmetric transfer of N-tosyl nitrene to  Molecules 2002, 7 903 olefinic double bonds in recent years [2], the most obvious precursors for chiral N-tosyl aziridines 1 are 2-amino alcohols 3 derived from natural or unnatural amino acids 4. Initially, compounds of type 1 have been prepared in mode