Oxaziridines

Introduction

An oxaziridine is a strained, three-membered ring, consisting of weakly bound carbon, nitrogen, and oxygen atoms. This heterocycle is synthesized by oxidation of the corresponding imine, most commonly with m-chloroperbenzoic acid. Also, reagents such as t-butyl hydroperoxide and urea hydrogen peroxide complex can be used.[1] Oxaziridines are very reactive due to the presence of three different atoms with different electronegativities. They can transfer the nitrogen or the oxygen atom and can undergo [3+2] cycloadditions. The high reactivity has been applied in many transformations with a wide range of reactants, such as sulfides, organometallic reagents, amines, and silyl enol ethers (Scheme [1]).[2] In this article, some examples have been selected in order to provide an overview of the recent synthetic achievements.

Scheme 1 Reactivity of oxaziridines

• References

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