Aziridines ring-opening reaction

Table 1 Contributions to aziridine ring-opening reactions...

Nitriles can act as nitrogen nucleophiles in aziridine ring-opening reactions. Two examples are shown in Scheme 25 in which a formal [3-1-2] cycloadduct is the final product. Tosylaziridine 147 was reacted with benzoni-trile and BF3 OEt2 catalysis to produce the r-fused imidazoline 148 <2004TL1137>. The utility of the reaction is limited in the case of cyclic aziridines to benzofused aziridines and either aryl or benzyl nitriles. It was also found that the reaction required stoichiometric BF3. Lesser amounts of Lewis acid reduced the chemical yield drastically. 

The aziridine ring opening reaction with phenol derivatives using copper(l) acetate (CuOAc)-DBU was reported by Li et al. [51]. Reaction of ethynyl nosyl-aziridine 170 and p-hydroxytyrosine derivative 169 in the presence of DBU (2 equiv.) and a catalytic amount... 

Table 7.1 Aziridine ring opening reaction with phenols in the presence of TBD (7)...

As for 2,3-epimines of the D-talo configuration, aziridine-ring opening reactions of A-tosylated epimine 296 with benzyl alcohol, benzyl amine, and a-toluenethiol have been reported in the literature." All of these reactions proceeded fra y-diaxially. 

In this review, the results of early studies in this area will be presented first in order to estabhsh the background and context of the recent studies of pyridinium salt photocychzation and bicychc aziridine ring-opening reactions. The overall aim of the presentation is to show how these processes can be used as key steps in synthetic routes to simple, yet interesting natural and non-natural products. 

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