Synlett 2013; 24(20): 2773-2774
DOI: 10.1055/s-0033-1338988
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© Georg Thieme Verlag Stuttgart · New York

Oxaziridines

Laura Buglioni
RWTH Aachen University, Institute of Organic Chemistry, ­Landoltweg 1, 52074 Aachen, Germany   Email: laura.buglioni@oc.rwth-aachen.de
› Author Affiliations
Further Information

Publication History

Publication Date:
14 October 2013 (online)

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.

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Scheme 1 Reactivity of oxaziridines
 
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