Carbohydrate aziridines

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. 

The aziridine-ring closure based on the Mitsunobu reaction, the Staudinger reaction, and isomerization of aminooxiranes also involves nucleophilic displacement as the key step of the reaction mechanism. Other reactions rarely reported in the synthesis of carbohydrate aziridines involve nonstandard, " even unusual procedures lacking a general application. 

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." ... 

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