Azirines synthesis

Azirines (three-membered cyclic imines) are related to aziridines by a single redox step, and these reagents can therefore function as precursors to aziridines by way of addition reactions. The addition of carbon nucleophiles has been known for some time [52], but has recently undergone a renaissance, attracting the interest of several research groups. The cyclization of 2-(0-tosyl)oximino carbonyl compounds - the Neber reaction [53] - is the oldest known azirine synthesis, and asymmetric variants have been reported. Zwanenburg et ah, for example, prepared nonracemic chiral azirines from oximes of 3-ketoesters, using cinchona alkaloids as catalysts (Scheme 4.37) [54]. 

There is one known exception to the trans nature of the addition a hindered polycyclic alkene where a cis addition occurs. More recently, small proportions of cis adducts have been detected as minor components in additions to cyclohexenes. An inmresting recem usage of the INs-alkene reaction is in the azirine synthesis of Scheme 87. ... 

Aziridines in the synthesis of azomethine ylides 89AHC(45)231. Aziridines in the synthesis of natural products 86AHC(39)I81. Azirines as intermediates in pyrrole formation 87KGS1299. 3-Amino-2-//-azirines, synthesis and properties 90KGS867. Ethynylaziridines 87MI6. 

Aivernhe, G., Lacombe, S., Laurent, A., Marquet, B. Addition of the Reformatskii reagent to azirines. Synthesis of 4-amino iactones. J. Chem. Res., Synop. 1980, 54-55. 

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