Aziridines, carbohydrate, reaction with

The purpose of this chapter is to present the chemistry of carbohydrate aziridines, with the emphasis being placed on surveying preparative methods and ring-opening reactions. We have omitted spiroaziridines and alditol-based aziridines from this chapter. Literature has been surveyed up to the end of 2003. The chemistry of carbohydrate aziridines has not yet been treated in a specialized article. 

A vast majority of the amino derivatives used as substrates in the synthesis of carbohydrate aziridines are A-substituted, mostly as A-acylamines or A-aryl(alk-yljsulfonylamines. Reaction of free amines has rarely been reportedin the carbohydrate field and difficult and incomplete cyclization was generally encountered. Paulsen and Stoye, however, reported spontaneous cyclization of 6-hydrazino-5-C-mesyl-D-hexofuranoses, obtained from 5,6-di-C-mesyl-hexofura-noses by treatment with hydrazine, into the A-amino-5,6-epimino derivatives." ... 

Herein an overview of the most relevant approaches for the synthesis of un-natiual heterocycles of biological and industrial potential from carbohydrates is presented the natiual heterocycles have been previously reviewed [6]. This review is hmited to heterocycles with one or more of their carbon skeletons derived from carbohydrate precursors—those formed by cycloaddition reactions are not included. Also, carbohydrates with strained ring systems, oxiranes, aziridines, and thiiranes have aheady been reviewed and are not included herein [20]. The synthetic approaches for the reviewed heterocycles are divided according to the size of the heterocychc rings and the number of hetero atoms in the ring. The bicyclic ring systems are included under the smaller ring of their skeleton. 

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